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Explore every episode of Rogue Startups

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Pub. DateTitleDuration
03 Nov 2023 RS292: Only the Most Important Things 00:11:26

Work smarter on things that really matter instead of working harder on things that make no difference. Today Craig talks about what he has learned about prioritizing, focusing, and honing in on tasks that really mean something. Between his professional experiences and input from his business coach, he’s learned that there isn’t a magic fix-all button that will bring in all the customers. Be critical of the time you spend on your business.

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. As always, if you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights:

  • Doing things for your business that make no difference
  • Does social media really impact your business?
  • Content marketing and SEO
  • Optimizing and focusing on one problem
  • One hundred steps that add up

Resources: 

Reach out on LinkedIn

Reach out on Twitter/X

Castos

Founder Insights

17 Nov 2023 RS293: The Risk Of Your Brand w/ Ed Freyfogle 00:39:03

Craig and Ed chat about all things bootstrapping, personal branding, social media, and growth trajectory. They also do a bit of catching up. Ed provides a unique perspective on these topics in addition to trying to convince Craig to move back to Europe.

Ed is the co-founder of OpenCage which provides a geocoding API (which converts geographic coordinates to locations around the world). He also organizes Geomob which is an event series (and a podcast) that meets in London, Barcelona, and Berlin. Geomob provides a relaxed forum for geoinnovation and for geospatial enthusiasts. He is also an angel investor (occasionally) whose interests include geo, API-based businesses, developer tools, aggregation, SaaS, and messaging, based out of Berlin, London, and Barcelona. 

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. As always, if you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights:

  • The story and vision behind OpenCage and Geomob
  • Ed’s “Business Card” Tab
  • Founders being active on social media
  • Branding should be about the company and not the founder
  • Promoting on LinkedIn and moving to Mastodon
  • The future of Twitter
  • Finding the balance of what you can share with the public and what to hold back
  • Being invested in a podcast/podcaster’s journey
  • The framework of successful in-person meetups and events

Resources: 

Ed Freyfogle

Ed on Mastodon

OpenCage

Geomob

Geomob Podcast

Castos

Founder Insights

27 Nov 2023 RS294: The Reality Of B2B SaaS Marketing w/ Corey Haines 00:47:34

On today’s episode, Craig chats with Corey Haines, founder of Conversion Factory. They chat about what it’s really like to be a B2B SaaS owner including how to handle marketing, if it’s necessary to learn the ins and outs of development, and how client work can kick you in the butt so you can stay fresh all the time.

Corey Haines is a marketing-first entrepreneur. He aims to help people with exceptional products, services, and content get the attention they deserve. Corey focuses on entrepreneurship, building a portfolio of small bets to optimize for autonomy, mastery, and purpose. He is currently running Conversion Factory, Swipe Files, and SwipeWell. He has worked with dozens of startups on marketing and growth including Cordial, Baremetrics, SavvyCal, Bonsai, Evercast, Riverside.fm, Holloway, Beamer, and Timetastic.

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. As always, if you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights:

  • Balancing client work with your own professional work
  • Working with a co-founder
  • How Conversion Factory helps their customers
  • Use cases and solutions pages
  • Package features together
  • “The More You Know, The Less You Know” Phenomenon
  • Staying engaged to stay fresh
  • Recognizing your own weaknesses so you can be stronger
  • The difficulties of coding and programming
  • Imposter syndrome and developing
  • Customer satisfaction and expectations
  • Always keep something in the pipeline for customers

Resources: 

Conversion Factory

Reach out to Corey on Twitter/X

Corey on LinkedIn

Corey’s Personal Site

Castos

Founder Insights

04 Dec 2023 RS295: SaaS Sales Masterclass with Matt Wolach 00:37:45

Matt Wolach is a genius at closing. Today, Craig gets the opportunity to pick Matt’s brain. They chat about why most people don’t close deals and what they can do to fix that. They wax poetic about outbound leads. How do you generate them? Where does it work best? Not to mention, they also talk about their social media processes.

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. And as always, if you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights:

  • Getting the next commitment before you hang up
  • The reason why most people can’t close
  • Generating outbound leads
  • Find your customers’ true problems
  • Land and expand strategy
  • Where and when outbound works best
  • Positioning yourself too low
  • Social media process
  • The importance of consistent value

Resources: 

Matt Wolach 

Follow Matt on Twitter/X

Connect with Matt on LinkedIn

Castos

Founder Insights

11 Dec 2023 RS296: Creating Great YouTube Hooks with Jake Thomas [YouTube Series] 00:48:17

Today Craig chats with Jake Thomas from Creator Hooks about what SaaS owners and entrepreneurs can do to catch the eye of possible customers and viewers on YouTube. Jake started his journey to Creator Hooks when he landed his dream job as a marketing manager at a fishing company. There, he learned the most important thing about creating titles and content for YouTube: modeling other successful YouTube videos. In today’s episode, Jake talks about that process as well as the importance of authenticity, posting on different social media platforms, and how to position topics in a way that will draw people in.

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. And as always, if you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights:

  • Building your YouTube channel without being someone you’re not
  • How older companies can stay trending: Edu-tainment
  • Types of content SaaS companies should produce
  • Competing in a saturated niche
  • Where to post different types of content on social media
  • Quick and dirty research tips
  • Quality versus Quantity
  • Positioning topics in an interesting way to get people to click
  • Topic and frame
  • How Creator Hooks can help you
  • Curiosity, Fear, and Desire
  • Split-testing thumbnails

Resources: 

Creator Hooks 

Reach out to Jake on Twitter/X

Castos

Founder Insights

18 Dec 2023 RS297: YouTube Channel Teardown with Josh Howard 00:45:41

Today’s episode is all about YouTube SEO. Craig is joined by Josh Howard, YouTube expert. Josh shares his knowledge about how to rank your video #1, and how to be successful in constructing a dynamic script and structure for your channel and individual videos. He also shows this information in action by analyzing Castos’ YouTube page, as well as Ahrefs’ YouTube channel.

Josh Howard started his analytics journey with website SEO before transitioning fully to YouTube. He used his love of math, statistics (and spreadsheets) as a foundation for understanding how to succeed on YouTube. He helps his clients make better content, utilize YouTube in valuable ways, and understand the analytics behind their videos to maximize the performance of their channels.

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. As always, if you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights:

  • People don’t go to YouTube to buy things, they go for free information
  • Where SaaS companies should put their YouTube content
  • Targetting search trends and potential
  • YouTube, the middle of the funnel
  • One keyword, one article, one time
  • The balance of evergreen and timely content
  • Analyzing Castos’ YouTube channel
  • Constructing YouTube playlists well
  • Keeping long-form content relevant 
  • Call to Action on YouTube videos

Resources: 

Reach out to Josh on Twitter

Connect with Josh on LinkedIn

Check out Josh’s personal website

Castos

Founder Insights

25 Dec 2023 RS298: 3 Steps To Move Your YouTube Channel To The Next Level with Trent Haire 00:42:38

Trent Haire drops some serious knowledge as he chats with Craig today about the three things that you can do to move your YouTube channel to the next level. Trent has years of experience and has worked with some major YouTubers by helping them go from little to no viewer and subscribers to thousands and even millions. In addition to his tips, they also talk about how B2B YouTube strategies differ from other YouTube channels, the importance of providing value first, and how YouTube stacks up to other social media platforms with shorter content.

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. And as always, if you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights:

  • How to get over the hurdle and start making videos
  • Setting good expectations
  • Making progress and improving is the main goal
  • B2B strategies and how they differ from others
  • “Hiding your vegetables”
  • Top of Funnel content and conversion 
  • YouTube versus LinkedIn versus Twitter/X
  • Providing value first
  • Discoverability and search versus suggested
  • Tracking the stats on your videos and updating the packaging
  • Long-form videos versus shorts
  • Three ways to bump your channel up to the next level

Resources: 

Creator Campfire 

Trent Haire on Twitter/X 

Castos

Founder Insights

12 Jan 2024 RS299: YouTube Scripting Done Right with George Blackman 00:49:38

George Blackman joins Craig in this installment of the Rogue Startups YouTube series. They chat about scripting episodes and what you can do to prepare yourself for making successful videos. George has had years of experience working with successful YouTubers who have had millions of views on their videos, in part because of George’s scripts. 

George and Craig also discuss why scripting is important, how to use a teleprompter, and the pros and cons of riffing versus being intentional and planning content. On the topic of AI, they focus on how he utilizes AI for title creation. One example of a prompt being:

“I am writing a video based on a topic and a “grand payoff” that I’ll provide below. Based on these two components, what emotional transformation will viewers have experienced by the end? (Related to the Grand Payoff)

Question/Topic: [insert here]

Grand Payoff: Viewers will understand XYZ.”

George is a consulting YouTube scriptwriter based just outside London. He has written scripts for creators like Ali Abdaal, Noah Kagan, Creator Booth, and Mike Shake. His new course (”YouTube Scriptwriter’s Playbook” Course) focuses on systemizing the process of scriptwriting to maximize retention. It starts on January 12th. Join in at a discount by using the code: launch10.

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights:

  • Improvising versus planned content
  • Find the key “punchy” moments from your notes
  • Sewing together mini-payoffs
    • Set-up, tension, and resolution
  • Start listicles with a punchy start, in the middle, and at the end
  • Thread in story elements and relevant personal anecdotes
  • How scripting saves time
  • Beginner teleprompter tips
  • George’s process for creating great videos:
    • Retention checklist: Information, progression, regression, and emotion
    • Creating and planning payoffs and tension
    • Repetition. Are you repeating information?
    • Clarity: conversational scripts that sound like yourself
  • AI and scriptwriting
  • YouTube versus Twitter/X
  • Tips for educational and informative videos
  • Analyzing your videos to create better content

Resources: 

George’s website

”YouTube Scriptwriter’s Playbook” Course Discount Code: launch10

Connect with George on Twitter/X

Castos

Founder Insights

19 Jan 2024 RS300: What’s Killing Google, and Exiting The Startup Phase 00:22:52

It’s the 300th episode of Rogue Startups, and it’s all about personal updates and professional improvements. Craig talks about where Rogue Startups started and what the future holds for this podcast and podcasting in general. What mediums will everyone gravitate toward this year? Who will win in this cage match between Google, YouTube, AI, SEO, and social media?

Craig also talks about where he wants to spend his time and energy in 2024. He has an ambitious but achievable goal of creating and publishing 200 videos on YouTube this year. Not to mention, he dives into this theory on personal engagement and personal content and how those things will change soon as well. Will they be more or less important? 

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights:

  • Evolving in the podcast industry
  • The difference between podcasting and YouTube
  • YouTube versus Google
  • What is the medium of the future?
  • AI trends and what that means for writers
  • Personal engagement and personal content
  • Diversifying beyond SEO content
  • The goal is optionality
  • Growth from the awkward teenage years to a mature adult
  • Building the right system and getting the right team

Resources: 

Castos

Founder Insights

31 Jan 2024 RS301: Why Brands Grow with Marc Thomas 00:47:59

One of the biggest lessons Marc Thomas learned about creating engaging content was the importance of bringing in bits of his personality. Today, Craig talks with Marc Thomas about how he has made a name for himself in the world of content and brand growth. Marc emphasizes what some of us forgot: B2B content has a purpose and we have to know what that purpose is. They also talk about the effectiveness of marketing “best practices,” the importance of transparency, Podia’s biggest marketing push and how it worked, and competitor landing pages.

Marc Thomas is the Senior Growth Marketer at Podia. Since 2014, Podia has been committed to building the most creator-friendly tools to help their customers sell online courses, digital downloads, membership subscriptions, and more to their audience.

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights:

  • The justification for B2B content: it doesn’t have to be boring and it has a purpose
  • Connecting your customers to a business outcome
  • How Podia created engaging, viral B2B content
  • Lessons from How Brands Grow by Byron Sharp
  • Vertical versus horizontal SaaS
  • Do marketing best practices really work?
  • Generosity and transparency
  • Competitor landing pages are insurance policies for your buyers
  • Continuing to learn and refine your craft
  • Balancing personal growth and playbooks
  • Failure is relative; people are adaptable

Resources: 

Marc Thomas, LinkedIn 

“How Brands Grow: What Marketers Don’t Know” by Byron Sharp

Castos

Founder Insights

19 Feb 2024 RS302: Beyond Content Marketing with Doug Cunnington 00:53:32

Doug Cunnington is an affiliate marketing, SEO, AI, and content marketing expert. Today, Craig and Doug chat about their experiences as founders and with web content, in hopes that they can learn from each other and pass along some tidbits of info to listeners.

AI-generated content is everywhere these days. The content marketing industry is split down the middle: they either embrace it or are pushing back. Is it worth it? Craig and Doug deep dive into their opinions on AI content, how they use it, and what the future of content marketing looks like. They talk about their cadence on YouTube and various other platforms. They also chat about exiting, retirement, and their paths now that they’re getting older.

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights:

  • Doug’s journey to content marketing
  • Position yourself so you don’t have to react immediately
  • The constantly changing industry of content 
  • The value of a content marketing strategy
  • AI-generated content 
  • Scripting for YouTube: shorter, tighter videos
  • Entrepreneurship and SaaS as you get older
  • Feeding the YouTube algorithm what it wants 
  • Content strategy differences between YouTube and podcasts

Resources: 

Doug’s YouTube Channel

Castos

Founder Insights

14 Mar 2024 RS303: After The Desert 00:13:33

In this solo episode, Craig talks through a recent mindset shift in the business.

https://youtu.be/vG0YKhAdPl0

Going from Zero to One you need to put out so many fires, and do so many things, and then in the growth phase you’re constantly trying new approaches, channels, messages, and levers. Here in the post-growth, calm phase, Craig’s found it a bit different to balance the Certainty and Uncertainty of running the business.

Craig’s also offering one-on-one founder coaching to SaaS founders looking to get from 0 to $3M ARR – head over to craighewitt.me/coaching to find out more and schedule a free consultation.

20 Mar 2024 RS304: What Is Google Doing?! (w/ Spencer Haws) 00:45:51

The world of SEO is changing at a rapid pace because of AI. How can we keep up? Can you still find, generate, and publish unique content online? The answer is yes. Google says that around 20% of online searches every day are ones they’ve never seen before. Here to talk about all that is SEO and keyword guru, Spencer Haws.

In this episode of the Rogue Startups Podcast, Spencer and Craig both talk about how they use AI and how human writers can work with AI-generated content. Spencer also gives his crystal ball prediction of what SEO will look like in the next five years. They also chat about where the platform of podcasting fits in the content world, face-to-face conferences and masterminds, and the reasons to stay with a business after receiving buyout offers. 

Spencer grew up in Mesa, Arizona, and moved to Richland, Washington. Because of the influence of his entrepreneur father and because he grew up during the dot com boom (and bust), he started dabbling in website creation in 2005. Since then, he has learned how search engine optimization works and how to best build and grow niche websites. The best way to contact Spencer with any questions or comments is here.

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights:

  • What is Link Whisperer and how will it help you
  • Is Rank Logic good for larger or smaller websites?
  • The best ways to use AI for content creation
  • Using AI for Listicles
  • SGE (Search Generative Experience) and SEO
  • Content development and marketing 
  • Separating your business from your life
  • How Spencer keeps up with the evolution of the industry
  • Books versus podcasts
  • The importance of conferences, masterminds, and business groups
  • To exit or not to exit, that is the question

Resources: 

Reach out to Spencer

Connect with Spencer on Twitter/X

Rank Logic

Link Whisper

Niche Pursuits

Castos

Founder Insights

27 Mar 2024 RS305: Validating SaaS In An Enormous Market w/ Christopher Gimmer 00:40:44

Is there such a thing as the perfect SaaS business? How are you creating your opportunities? Are you focusing on your end goal for your business? Today, Craig is joined by Christopher Gimmer from Snappa and Good Metrics. Chris talks about his path, which led him to founding multiple businesses and a successful exit. He dives into his decision-making process and how he finds his next big opportunity. As entrepreneurs who have 100% bootstrapped their businesses, Craig and Chris talk about their processes, successes, and lessons they have learned on their journeys.

It can be hard to realize, narrow down, and make big-picture decisions for your company, especially if you’ve built it yourself. Yes, it is your baby, but it’s important to realize when to let go and when to grasp new opportunities.

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights:

  • Learning about best practice business models from previous endeavors
  • Expansion revenue vs low churn
  • The importance of keeping focused on business goals. Acquisition? Expansion? 
  • How Chris finds, makes, and determines new opportunities
  • Pricing and business models
  • How to be business-critical
  • Naming: when to bite the bullet
  • The status of Good Metrics
  • Marketing and differentiating yourself from your competition
  • Horizontal vs Vertical SaaS businesses

Resources: 

Find Chris on Twitter/X

Christopher Gimmer

Nathan Berry’s article, “Direct Sales for Bootstrapped SaaS Startups: from $1,300 to $725,000 MRR

Castos

Founder Insights

03 Apr 2024 RS306: YouTube Growth Secrets w/ Aaron Francis 00:42:33

Making it big on any social media platform can be an arduous journey. You have to worry about your equipment. What looks good? What content is interesting right now? How do I get people to find me? YouTube has its own brand of problems too. How long do you make videos? What should the thumbnail look like? To script or not to script; that is one of many questions.

On today’s show, Craig welcomes Aaron Francis, software developer, content creator, and YouTube genius. Craig picks Aaron’s brain about his best practices when it comes to making videos and other content. They talk about what makes YouTube so special in the social media world. Not to mention, Aaron voices his opinion on personal brands. Loyal listeners already know Craig’s opinion. #TeamPersonalBrand

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights:

  • Why choose to put your efforts into YouTube rather than other mediums
  • Different formats of video which will make you stand out
  • How podcasting works within a marketing plan
  • Overcomplicating your tech when you should focus on your content
  • Best practices and focuses that have worked well for Aaron
    • Understanding the pattern of content that works for YouTube
    • Adapting to the platform is important
    • Take a piece of content and wrap it in something more interesting and clickable
    • Have an angle, not necessarily a unique angle
    • With every video, make it feel like it’s your first video and no one knows you
  • The difference between content on YouTube versus other platforms
  • What Aaron has been up to lately
  • The power of a personal brand
    • A personal brand is valuable in general

Resources: 

Try Hard Studios

Connect with Aaron on Twitter/X

Castos

Founder Insights

10 Apr 2024 RS307: Doing Less and Doing It Better 00:18:45

Learning valuable lessons on your journey to success can take a while. Today, Craig shares his insights on this topic as it correlates to Castos and to his goal of creating 200 episodes in 2024. (Spoiler alert: things are going well for him.)

Sometimes the hardest thing to do is to say no to something. As entrepreneurs and bootstrappers, we have ambitions and goals, but it’s not always feasible to say yes to everything you want to do. Those of us working in a micro-SaaS business can find more success by niching down and focusing all our efforts on making one great product or service. So…

Are you niched down as much as possible?

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights:

  • Updates on Craig’s goal of 200 episodes goal
    • Gear fatigue and indecision
    • Finding a recording setup and format that works for you
    • Interviews versus solo episodes
    • The difficulties of video over audio content
  • Founder Minimalism
    • Doing well with one thing
    • Diversifying your products or services
    • Fighting the urge to do everything
  • Utilizing and building a personal brand
    • Indirect impact on you and your business
    • Making what you want to do a little easier
    • The steps to build and bolster your personal brand

Resources: 

Follow Craig on Twitter/X

Castos

Founder Insights

17 Apr 2024 RS308: Programmatic SEO with Stuart Brameld 00:37:44

Creating content that will engage readers and appease the algorithm gods is a difficult task. That’s where Stuart Brameld comes in. He is here today to share his insights on growth, marketing, programmatic SEO, and content creation with Craig and the Rogue Startup listeners. He also talks about how Growth Method can help your company grow and gives tips on how to effectively use AI to help you create perfectly worded web content.

What is Growth Method? When should you use AI when creating content? What is programmable SEO?

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!

When should you use AI when creating content? What is Growth Method? What is programmable SEO?

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights:

  • What Stuart and Growth Method does for their clients
  • Adopting a growth and experimentation approach to marketing
    • Stuart’s definition of experimentation in terms of company tasks
  • What you can do if you don’t have enough data for meaningful testing
    • Decisions made without supporting data
    • Don’t post content and forget about it
  • Moving through stages in the design and planning phases
  • Programmatic SEO powered with AI
    • Case study: review site
  • Going from a spreadsheet to WordPress
  • Making mistakes when posting content
    • Posting a lot of content at once
  • Improving the design and aesthetic of content after the baseline is in place
  • Tips for using AI for content creation
    • Using custom instructions 
    • Finding an AI coach (if you’re interested, send Craig a message)
    • AI versus hiring writers
    • Top-of-funnel content
  • What to be aware of when you’re working with programmatic SEO

Resources: 

Growth Method

Reach out to Stuart on Twitter/X

Stuart on LinkedIn

Follow Craig on Twitter/X

Castos

Founder Insights

24 Apr 2024 RS309: Growth Fundamentals Most Founders Get Wrong 00:42:14

Alison French joins Craig behind the mic today to talk about ICP and go-to-market strategy, as well as the challenges that bootstrap founders have. We can all overcome these struggles with the right tools, systems, outlook, and determination. She commiserates with Craig about what bootstrappers have to go through and also gives some great advice for new startups and entrepreneurs. 

Alison runs a boutique sales and marketing consultancy all around B2B SaaS startups. She is the Marketing Gal who got bit by the revenue bug and became passionate about helping companies scale their revenue by focusing on the intersection of sales and marketing. With over 20 years of experience in the field, she specializes in assisting B2B founders and leaders who venture into new markets. Her ultimate goal is to help you build a robust sales and marketing infrastructure that not only streamlines lead generation but also maximizes your ability to close deals. And the best part? She does all this while keeping your expenses to a minimum.

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights:

  • Why everyone sucks at execution.
    • Ideas are cheap. Execution is the hard thing.
    • Recognize how to get out of your own way and when to delegate
      • How can you delegate cheaply
      • Free up your time so you can do the higher-leverage tasks
    • Getting good content writers and/or a copy editor
      • The entire team needs to know the values and priorities of the company
  • People discount the importance of brand research and focus
    • ICP: marketing, content, 
  • When you’re taking a dollar of profit and reinvesting in growth, where do you focus?
    • Build a prospect list and then proactively nurture that small segment
    • Versium: matched audience media
    • The importance of retargeting
    • Your Dream 100
    • Cold E-mail: a balance of who you can go after, the right time, and the right place
  • Starting your bootstrapped B2B business today: where do you focus?
    • Look at your prospects, laser focus on your ICP
    • Recognizing you can’t do it all
      • Look at your tech-stack
      • Know, instantly, who you can delegate to
      • Throw tasks out into the world and see what happens
      • As a founder, you’re never going to find someone who can sell as much as you

Resources: 

Alison French, LinkedIn

LTO.com 

Follow Craig on Twitter/X

Castos

Founder Insights

01 May 2024 RS310: Stealing Customers 00:13:26

In this solo episode Craig talks through a few updates from Castos, how he’s thinking about growth, and where he’s focusing his attention and energy in the business.

Craig also gives an update on his personal content: this podcast, his Founder Insights newsletter (check it out at craighewitt.me/join ) and his new 1-on-1 coaching business.

Craig’s started coaching founders, 1-on-1, to help them grow, stay sane, and thrive in their business.

If you’re a SaaS founder and are looking for a sounding board, someone who’s seen a lot in business, and has your back (through thick and thin) head over to craighewitt.me/coaching to learn more and schedule a free 30-minute session. The coaching has been really rewarding, and is a great way to give back to the founder community that has given him so much.

If you’re interested in sponsoring Rogue Startups, hit me up on Twitter/X at twitter.com/thecraighewitt

08 May 2024 RS311: Does Your Business Pass The Test? 00:45:30

Join Craig as he chats with Dan Andrews, renowned cohost of the Tropical MBA, a weekly podcast dedicated to bootstrapping businesses and entrepreneurship. Dan is also the founder and brains behind Dynamite Circle and Remote First Recruiting.

Today, they’re dishing out some expert advice about podcasting, content creation, and strategies for acquiring customers. Tune in to explore Dan’s opinions on the rapid evolution of AI and his tips on building thriving ventures.

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights from Craig and Dan’s conversation:

  • Dan’s podcasting inspirations and his journey into the industry
  • Why Dan chose podcasting over any other platform
  • Is YouTube worth the effort?
  • Finding the overlap between creativity and growth
  • The importance of Investing in your team and treating your business like an investment
  • Getting over imposter syndrome and what your job is as an entrepreneur
  • Creating successful businesses versus businesses that are “just okay”
  • The difficulty of getting to $1 mil for a SaaS company
  • The lifecycle of the entrepreneur ecosystem
  • Predictions for bootstrapping and podcasting trends in the next 5 years

A Little About Dan and TropicalMBA:

Tropical MBA started in 2009 when hosts Dan and Ian wanted to meet other entrepreneurs for some celebration and commiseration. Most of their first episodes were just them, sharing what they learned about bootstrapping their own business until they concluded that journey with a multi-seven-figure exit. Both Dan and Ian have moved on to their next projects but continue to talk with entrepreneurs on their show.

Links & Mentions from This Episode:

Tropical MBA

Connect with Dan on Twitter/X

Lifestyle Business Podcast

Internet Business Mastery

Smart Passive Income Podcast

Startups for the Rest of Us

Profit First: Transform Your Business from a Cash-Eating Monster to a Money-Making Machine” by Mike Michalowicz

Check out Matt Paulson’s Twitter/X

“Exploitative Play in Live Poker: How to Manipulate your Opponents into Making Mistakes” by Alexander Fitzgerald

Rogue Startups Resources:

Follow Craig on Twitter/X

Castos

Founder Insights

15 May 2024 RS312: Hacking LinkedIn 00:38:19

In today’s episode, Craig is joined by Adam Shaw from Marketing for Founders to talk about precise and overarching marketing strategies. Adam’s expertise lies in navigating Reddit and LinkedIn, two social media platforms that B2B SaaS entrepreneurs often neglect. Together, they explore Adam’s techniques for Reddit, LinkedIn, and broader marketing principles. Should you focus on active marketing or passive marketing? How do you know how much time to put into marketing? What are good marketing strategies for new business owners? Check out this episode for the answers to these questions and more.

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights from Craig and Adam’s conversation:

  • Utilizing your Reddit page as a landing page for your business
  • Optimizing LinkedIn as a platform to maximize its potential
  • Identifying which companies are suited for each social media platform
  • The Marketing for Founders service and model
  • Recognizing the flexibility inherent in marketing strategies; it’s not one size fits all
  • Consistency is the key to seeing results from marketing
  • When to engage in active marketing versus passive marketing
  • How much time should you spend on marketing?
  • When you should do your marketing on your own versus when to hire a marketer
  • Find where your customers are hanging out
  • Identifying the two biggest obstacles that might be impeding your scalability efforts

A Little About Adam:

Adam’s goal and vision for Marketing for Founders is to help B2B SaaS founders do their own marketing.

Links & Mentions from This Episode:

Marketing for Founders

Adam Shaw’s LinkedIn

The Marketing Memo

LinkedIn Sales Navigator

Gummy Search

Hive Index

Sparktoro

Rogue Startups Resources:

Follow Craig on Twitter/X

Castos

Founder Insights

22 May 2024 RS313: Unfair Advantages with Jason Cohen 00:59:40

This episode is sponsored by ChurnKey: Optimize your company’s retention and supercharge growth with Churnkey.

Are you looking to fuel your startup’s revenue growth? Jason Cohen, founder of WP Engine, joins Craig behind the mic on this episode of Rogue Startups. Join Jason and Craig as they delve into strategies for sustained revenue growth, even when certain metrics plateau. Discover the power of pricing strategies and delivering enhanced value propositions to justify premium prices. Learn how diversifying variables beyond product features can make your business highly desirable to your market.

Moreover, Jason emphasizes the pivotal role of the community in authentic company development. Uncover the importance of leveraging existing assets and explore his innovative “adjacency matrix” method for strategic expansion.

Got any thoughts on our content or ideas for upcoming episodes? Reach out to Craig via email at podcast@roguestartups.com. If you’ve found our podcast valuable, don’t hesitate to share it with others. If you could spare a moment, leave us a review on iTunes. We appreciate your support and look forward to connecting again next week!

Highlights from Craig and Jason’s conversation:

  • Determining success or failure as a founder and business owner
  • Strategies for becoming the market leader in your industry
  • Importance of building a community to enhance customer value
  • Distinguishing between brand, company culture, values, and mission
  • Identifying when branding becomes crucial for a startup’s success
  • Deciding between staying focused on your core business or expanding into new ventures
  • Embracing a culture of innovation despite the risk of failure
  • Achieving a balance between personal fulfillment, skill development, and company needs
  • Practical applications of AI for internal operations and enhancing customer experience

A Little About Jason:

With over 27 years of experience in business and software development, Jason Cohen is the founder of WP Engine where he has served in several roles including CEO, Head of Engineering, Head of Product, and CTO. Jason Cohen is the Chief Innovation Officer at WP Engine, with a focus on the intersection of corporate and technology strategies as well as continue as the company’s executive sponsor for the headless platform, Atlas. Jason is a serial entrepreneur, having built four technology startups to more than $1 million in annual revenue. He is a founding member and mentor at Capital Factory, and was previously a founder of Smart Bear and IT WatchDogs. Jason received the EY Entrepreneur Of The Year 2017 Central Texas Award for Technology.

Links & Mentions from This Episode:

WP Engine

Jason on Twitter/X

Jason’s Blog

Rogue Startups Resources:

Follow Craig on Twitter/X

Castos

Founder Insights

29 May 2024 RS314: The 8 Attributes Of A Perfect SaaS Business 00:21:04

Optimize your company’s retention, and supercharge growth with Churnkey.

Are you looking to build the perfect SaaS business? Discover the key elements for crafting a thriving SaaS venture in the latest Rogue Startups episode. Craig delves into the success story of Castos, dissecting eight crucial attributes essential for any SaaS business to flourish. Some of these are things Castos has nailed, and others are not. Craig candidly shares insights from personal and professional growth and extensive research.

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights from this episode:

  • Optimal pricing strategies for maximum profitability
  • Enhance retention by ensuring that your product or service is exceptionally sticky
  • Incorporate payment solutions seamlessly into your business to enhance user experience
  • Become a valuable asset for your clients by contributing to their revenue streams
  • Implement strategies to heighten switching costs, fostering customer loyalty.
  • Customers should be getting value even when they’re not actively using your product
  • Stand out from competitors by highlighting unique features and advantages
  • Confirm market demand by researching your niche

Links & Mentions from This Episode:

Designing The Ideal Bootstrapped Business – Microconf talk

Rogue Startups Resources: 

Follow Craig on Twitter/X

Castos

Founder Insights

05 Jun 2024 RS315: $8 LinkedIn Ad Leads 00:46:53

Optimize your company’s retention, and supercharge growth with Churnkey.

In this episode Craig sits down with Matt Hayman from Linklo to talk through how we as SaaS founders can set up cost effective LinkedIn ads.

Matt has strong experience in building B2B lead flows for a variety of companies, and out of that experience saw the pain for a more customizable LinkedIn ads experience.

In the episode Matt breaks down his formula for a 3-step ad sequence that consistently gets him and his clients leads from LinkedIn for less than $8.

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights from Craig and Matt Hayman’s conversation:

  • Ways that you can think of LinkedIn from a high-level conceptual standpoint
  • Maximizing lead generation with cost-effective LinkedIn Ads
  • Enhancing Brand Identity and Effectiveness Strategies
  • The importance of clarity on ICP (ideal customer profile)
  • Building emotional connections with prospects is the key to succession engagement
  • The goldmine of opportunity from the prospects that come from early calls
  • How Linklo can help you and your company
  • What you bring to the table and how your personality manifests in your demos

A Little About Matt:

Matt knows LinkedIn Ads. Founder of Linklo.io. He’s passionate about changing the way agencies and advertisers manage LinkedIn Ads at scale. 

Links & Mentions from This Episode:

Matt Hayman on LinkedIn

LinkLo

Rogue Startups Resources: 

Follow Craig on Twitter/X

Castos

Founder Insights

12 Jun 2024 RS316: Getting 100k LinkedIn Followers 00:43:16

Optimize your company’s retention, and supercharge growth with Churnkey.

In today’s episode, Craig welcomes Sam Browne. They take a deep dive into the ever-evolving landscape of LinkedIn, the premier platform for professionals seeking to expand their network and amplify their influence.

With Sam’s expert advice and practical tips, they guide listeners through proven strategies for personal branding, lead generation, and relationship building. Tune in as they tackle pressing questions like content recycling, imposter syndrome, and the future of video on LinkedIn. Whether you’re a seasoned LinkedIn aficionado or a newcomer eager to make your mark, this episode promises invaluable insights to propel your career forward.

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights from Craig and Sam’s conversation:

  • LinkedIn is where the money is when it comes to social media.
  • Regarding topics to post on LinkedIn: choose a primary niche but don’t shy away from others you are interested in because that contributes to your personal brand.
  • Because social media is so transient, should you recycle content every 90 days?
  • Treat LinkedIn as more than just lead generation and make CTAs low-friction.
  • How to overcome imposter syndrome: you’re not alone.
  • Observe and analyze the feedback and comments you receive.
  • Commenting versus posting: where should your focus go?
  • The different personas we adopt on various social media platforms.
  • The best way to build relationships on LinkedIn.
  • Craig’s 30-Day LinkedIn Gameplan.
  • Steps to best optimize your LinkedIn profile.
  • Video is the future on LinkedIn and other forms of social media.

A Little About Sam:

Sam has over 100,000 followers on LinkedIn. He’s a lifestyle entrepreneur and a growth and income LinkedIn expert. He loves to help entrepreneurs grow their audience and generate income on LinkedIn. He works with clients about anything and everything regarding LinkedIn, from optimizing profiles to creating great content ideas to forming a brand that stands out.

Links & Mentions from This Episode:

Sam on LinkedIn

Sam Browne

Rogue Startups Resources: 

Follow Craig on Twitter/X

Castos

Founder Insights

19 Jun 2024 RS317: Steal My LinkedIn Growth Strategy 00:18:45

This episode is sponsored by Clearly Design. Francois and his team at Clearly Design are absolute geniuses of UI, UX, and design. If you’re looking to level up your design, UI, and UX give Clearly Design a try

If you’re running a B2B business today, chances are that LinkedIn is a fantastic growth opportunity for you, and your business.

But if you’re looking at the vastness of how to grow your audience (and business) on LinkedIn, and feel overwhelmed, you’re in luck.

In this solo episode I’m breaking down my entire LinkedIn content and growth strategy.

You can take and implement this strategy to grow your personal brand, get more exposure of your message to your Ideal Customer Persona, and get highly qualified leads for your business as a result.

03 Jul 2024 RS318: LinkedIn Content That Converts 00:44:17

Clearly Design works in every aspect from branding to marketing, from product to promotion. Go to Clearly.Design for a discount on his monthly design subscription service.

Today Craig is chatting with Nemanja Zivkovic about conversion on LinkedIn. This is the crux of LinkedIn for a lot of us, as B2B SaaS founders, especially indie or bootstrapped businesses. So how do you find opportunities on LinkedIn for you? How do you use LinkedIn to drive more engagement, resulting in deals and dollars?

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights from Craig and Nemanja’s conversation:

  • Common objections to being more active on LinkedIn
  • The narrative, structure, and intention behind LinkedIn engagement and posts
  • Differentiating yourself with unique points of view and varied content on LinkedIn
  • B2B: Solving problems instead of selling
  • Building trust on LinkedIn through diverse post types
  • How engagement fosters relationships and leads to conversions
  • Using feedback forms to understand customer origins
  • Fast-tracking responses with templates (no automation)
  • Maximizing company synergy in LinkedIn posts
  • Ensuring visibility by reaching out to expand your network’s reach

A Little About Nemanja:

Nemanja started as a strategist and began with a startup where he served as CMO, repeating this role across various sectors. His experience spans from COO roles with heightened responsibilities to founding his company in 2020. This diverse exposure has shaped his unique perspective on B2B growth, blending B2C insights to fill industry gaps.

Links & Mentions from This Episode:

Nemanja on LinkedIn

Funky Marketing Podcast

Lead Delta

Authored Up

Expandi

Dripify

Rogue Startups Resources: 

Follow Craig on Twitter/X

Castos

Founder Insights

17 Jul 2024 RS319: Mastering LinkedIn Video Content 00:50:21

Clearly Design works in every aspect from branding to marketing, from product to promotion. Go to Clearly.Design for a discount on his monthly design subscription service. Tell him that Rogue Startups sent you.

Danny DelVecchio joins Craig today to discuss creating, posting, and uploading video content on LinkedIn. In today’s conversation, you’ll discover how to overcome challenges in creating compelling video content, even if you lack confidence on camera. Uncover the essentials of selecting the right gear to kickstart your video journey and crafting timeless content across various platforms. Gain insights into balancing visual appeal with clear messaging and discover influential LinkedIn users worth following.

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights from Craig and Danny’s conversation:

  • Tips for creating videos when your on-camera presence is lacking
  • Why people don’t create video content on LinkedIn
  • Essential gear and tools for getting started with video
  • Creating evergreen content across multiple platforms
  • Choosing assistants and social media managers
  • What happens when  you overemphasize graphics over your message
  • Top LinkedIn users to learn from
  • Batching recording sessions each week/month
  • Maximizing engagement with LinkedIn connections
  • Look for things that people are excited about and start conversations about it
  • Three styles of video everyone should be creating: educational content, content that builds trust, and sales content

A Little About Danny:

Danny elevated founders with social video. He is also a father, husband, business owner, and coach.

Links & Mentions from This Episode:

Danny DelVecchio on LinkedIn

Danny DelVecchio on YouTube

Alex B Sheridan on LinkedIn

Chris James on LinkedIn

Laura Acosta on LinkedIn

Rogue Startups Resources:

Follow Craig on Twitter/X

Castos

Founder Insights

24 Jul 2024 RS320: The Psychology of Sales 00:43:26

Clearly Design works in every aspect from branding to marketing, from product to promotion. Go to Clearly.Design for a discount on his monthly design subscription service. Tell him that Rogue Startups sent you.

What gets someone to buy our products or services? How do you make LinkedIn a meaningful sales channel? In today’s discussion, Craig speaks with LinkedIn expert Ryan Musselman on optimizing your LinkedIn presence. Ryan highlights the importance of focusing on and mastering a single platform for maximum impact. Understanding effective methods to connect with a broad audience is crucial for achieving your strategic goals. LinkedIn offers excellent opportunities to engage with your target demographic.

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights from Craig and Ryan’s conversation:

  • What influences customers to buy services and products
  • What if customers don’t know what they want?
    • The answer to what they need is inside of them, so ask good questions
  • Selling the path to the outcome and the transformation
  • Focus on helping potential and current customers overcome their obstacles
  • Have a natural way to sell without “selling”
    • Speak to the problem or the want instead of using the phrase “demo”
  • Maximizing the time you spend on LinkedIn
  • The more rapport you build with a potential customer, the more they will trust you
  • Engaging with their content in order to create deeper connection rates
  • LinkedIn as a platform is embracing video more and more
  • LinkedIn as an amplification system
  • The power of video for building connections
  • Be intentional with  LinkedIn for 6 months: engage with content, make connections, and build relationships.

A Little About Ryan:

Ryan Musselman is the founder of Coaches who Close. CwC equip coaches to close, scale, and enterprise with new clients, content engines, and constant lead flow.

Links & Mentions from This Episode:

Ryan on LinkedIn

Rogue Startups Resources:

Follow Craig on Twitter/X

Craig on LinkedIn

Castos

Founder Insights

31 Jul 2024 RS321: B2B Lead Gen on LinkedIn 00:47:30

If there’s one thing Craig loves more than podcasting, it’s sales.

In this episode, he shares his enthusiasm with tech sales coach Peter Ahn. They discuss everything from bridging the gap between creating content and driving leads to the importance of being genuine and authentic.

Peter drops plenty of knowledge bombs, so grab a chair, take out a notebook, and jot down some great tips from this episode of the Rogue Startups podcast.

Highlights from Craig and Peter’s conversation:

  • Why are technical founders so scared of tech sales
  • The trigger that helps tech founders understand sales
  • Earning the trust of your customers and helping them gain confidence
  • Staying up-to-date with authentic sales strategies
  • Dealing with imposter’s syndrome
  • Which businesses benefit most from LinkedIn for lead generation
  • Make your world ubiquitous for potential customers
  • Creating content creation that will generate leads

A Little About Peter:

Peter is a Korean-American tech sales coach and former VP with experience at Twingate, Front, Slack, Dropbox, and Google, he is passionate about sharing his authentic experience as an Asian-American while helping others find their own unique sales voice.

Peter knows that sales is becoming increasingly difficult, so developing an “edge” or advantage requires combining effective skills and confidence in one’s identity. He coaches on both of those topics.

Links & Mentions from This Episode:

Peter on LinkedIn

Peter Ahn website

Rogue Startups Resources: 

Follow Craig on Twitter/X

Craig on LinkedIn

Castos

Founder Insights

07 Aug 2024 RS322: Marketing, in 2 hours a week 00:16:17

In this episode Craig descirbes his current SaaS marketing approach. Balancing Active and Passive marketing, he’s got his marketing time down to just a few hours a week. Using a video-first, AI-assisted workflow he’s reaching his target market, educating his prospective customers, and building goodwill in the community.

14 Aug 2024 RS323: Breaking Through Plateaus with Josh Ho 00:51:33

Today on the Rogue Startups Podcast, Craig chats with Josh Ho from Referral Rock about the peaks and valleys of being a founder. When is the right time to sell? Is there ever a right time? How do you break through a plateau in your business growth? How do you switch from wearing your visionary hat to your marketing and sales hat? They also do a deep dive into when and how you should go about delegating tasks so you can focus on more important things.

Josh built Referral Rock from the ground up. Referral Rock helps customers run end-to-end referral programs with frictionless sharing, nudge reminders, and rewards customers actually care about. They help bring in more referrals from happy customers — through a remarkable referral experience — without the pain of building & tracking it all yourself.

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights from Craig and Josh’s conversation:

  • Switching from visionary mode to marketing mode
  • Reflecting on decisions made as a founder
  • Letting go of your inner Superman: letting your team handle sales
  • Knowing what you need and being strong enough to look for help
  • Strong operations is speed
  • The importance and effectiveness of SEO today
  • Valuating your business and progress
  • Growing, selling, and the future of your business
  • “Good enough” versus “Being done”

Links & Mentions from This Episode:

Referral Rock

Josh Ho on Twitter/X

Josh Ho on LinkedIn

Rogue Startups Resources:

Follow Craig on Twitter/X

Craig on LinkedIn

Castos

Founder Insights

21 Aug 2024 RS324: $100 Million Bootstrapped SaaS with Adam Robinson 00:41:34

In this episode of the Rogue Startups podcast, Craig sits down with Adam Robinson to explore key topics such as founder psychology, overcoming self-limiting beliefs, and avoiding self-sabotage. They delve into how to identify and break free from the plateau and gradual decline that can occur when you believe you have achieved product-market fit but haven’t. Adam, who has built multiple successful businesses, shares his valuable insights and practical tips with Craig. Don’t miss out—tune in to gain actionable advice from an experienced entrepreneur!

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights from Craig and Adam’s conversation:

  • The success story behind Adam’s unicorn B2B SaaS business
  • An in-depth exploration of achieving product-market fit
  • The importance of establishing effective business processes
  • How to avoid the entrepreneurial trap: recognizing when to transition to a new venture
  • The story behind “2,300 sign-ups and 13 paying customers, 6 weeks after launch”
  • How Adam deals with bad press when he pushes the envelope
  • The future of data privacy and cookies
  • Creating value for customers and learning from mentors and successful entrepreneurs

A Little About Adam:

Adam is the CEO of Retention.com. Retention.com is the industry-leading Shopify e-commerce solution for increasing revenue. They enable email-based retargeting so brands can re-engage lapped audiences and grow their email lists for the future. On the outside, Retention.com is a magic wand that makes money fall from the sky. He also runs RB2B, a website that helps identify your anonymous website visitors.

Links & Mentions from This Episode:

Adam Robinson, LinkedIn

Retention.com

RB2B.com

Rogue Startups Resources:

Follow Craig on Twitter/X

Craig on LinkedIn

Castos

Founder Insights

30 Aug 2024 RS325: Stuck? Ask Yourself These 3 Questions 00:10:00

Are you a SaaS founder feeling stuck, unmotivated, or unsure about your next move? In this video, I dive into three powerful questions that can help you break through mental barriers and gain clarity on your business’s direction.

These thought-provoking questions will challenge you to confront hard truths, think like an outsider, and tap into your own wisdom. Whether you’re just starting out or scaling up, these insights will help you refocus and reinvigorate your entrepreneurial journey. Don’t miss this opportunity to gain a fresh perspective on your SaaS business!

04 Sep 2024 RS326: 5 Things Most Founders Struggle With 00:19:12

Today’s a solo episode with Craig where he’s talking through the 5 common topics and themes that he helps most of his coaching clients through.

Whether it’s through his 1:1 coaching with private clients or in serving as Advisor In Residence at TinySeed, where he’s advised over 50 SaaS founders, a few common patterns have emerged.

These topics include:

  • Managing Uncertainty
  • Getting a Sanity Check On New Initiatives
  • Being An Accountability Partner
  • Navigating Financial Troubles
  • Sales & Marketing Strategy

Most important thing to remember from this is that being a founder is tough, but you are not alone. Text a friend, join a community, get a coach, but somehow build that support network around yourself so that you can thrive as a founder to grow your business.

If you’re interested in learning more about my one-on-one founder coaching head over to craighewitt.me/coaching – I offer free 30 minute consultation sessions, and if we’re a good fit to work together we can go from there.

11 Sep 2024 RS327: 3 Traits Of Successful Founders w/ Rob Walling 00:44:07

Craig has TinySeed’s Rob Walling in the hot seat today. They’re chatting about defining, attaining, and maintaining success. What does success mean to you? How do focus, clarity, and execution fit into it? Rob, a leading founder and one of the most successful entrepreneurs in the SaaS industry, shares his expert advice and insights on achieving success.

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights from Craig and Rob’s conversation:

  • What makes Rob Walling a successful founder
  • How to gain clarity and focus in your decision-making
  • Relentless execution: why the winners are those who practice every day
  • Intrinsic vs. extrinsic motivation
  • Creating a network of accountability
  • The parallels between “fitness” and being a founder
    • Making success fun
    • Finding someone to hold you accountable
  • Is there a one-stop shop for founders?
  • The layers of Rob’s business model funnel

A Little About Rob:

Rob Walling is the founder of TinySeed, host of Startups For The Rest Of Us, and of MicroConf. Rob has bootstrapped multiple startups to exit, most recently Drip. He has been advising, mentoring, and investing in startups for more than a decade. He has also written The SaaS Playbook which aims to help entrepreneurs strategize and build frameworks from the trenches so they can grow successful SaaS companies.

Links & Mentions from This Episode:

saaslaunchpad.co

Rogue Startups Resources: 

Follow Craig on Twitter/X

Craig on LinkedIn

Castos

Founder Insights

18 Sep 2024 RS328: Are you Productive or Effective as a founder? 00:14:27

Running a business is both incredibly rewarding and exhausting. Over the years, I’ve experienced highs of motivation and productivity, but I’ve also hit those low points, battling burnout and loneliness. In this post, I want to share some of the habits, strategies, and mindset shifts that have helped me stay in the game and maintain the discipline and accountability necessary to keep moving forward. If you’re a founder—or on any long-term entrepreneurial journey—I hope these insights can help you do the same.

Watch on YouTube

The Isolation of Being a Founder

Being a single founder can be a lonely journey. For me, working from home, with my wife and kids out for the day, often leaves me in the company of my dog and cats. While solitude has its perks, isolation can be damaging to both motivation and productivity.

  • Find Community: Join a mastermind group or work from a co-working space. Being around people, even casually, can be a game-changer. I started playing tennis twice a week—not because I’m a tennis fanatic, but because it gives me a social outlet and some physical exercise. Finding balance between work, family, and social time is key to staying mentally sharp.
  • Surround Yourself with Peers: Programs like TinySeed or the DC Accelerator not only offer education but surround you with like-minded individuals who push you to level up. In my career, the periods when I’ve had a strong community around me have been my most productive.

Accountability: The Secret Weapon for Consistent Progress

One of the biggest myths in entrepreneurship is the idea of the “solopreneur” doing everything on their own. The reality? Success comes from being accountable, whether it’s to your team or an external source.

  • Accountability to Your Team: I’ve got payroll to meet, and employees who count on me. That creates built-in accountability. But even if you’re a one-person operation, you need some form of this. Whether it’s a peer accountability partner or joining a program with structured check-ins, having someone who will ask, “Did you get that done?” is crucial.
  • Accountability Buddy: Inspired by a conversation with Rob Walling, I decided to create My Founder Pal, an accountability network for founders to check in with each other regularly. It’s still in its early stages, but the idea is to create a system where we set goals and follow up on progress, offering each other the motivation to keep pushing forward.

Daily Structure for Focus and Efficiency

One simple habit that has had a huge impact on my productivity is making a list of three things I need to get done each day. I literally put the notebook on my keyboard so it’s the first thing I see before starting my day. These can be small tasks, but they are important things that move the needle. I prefer to write the list in the morning so I have a fresh perspective on what matters most that day.

This simple act keeps me focused on what’s essential, rather than getting distracted by Slack or email first thing in the morning. It’s about prioritizing effectiveness over productivity—doing what matters most rather than just doing more things.

Sharing Your Work

Another aspect of accountability that I’ve found useful is sharing my work with my team. Whether it’s a new YouTube video or an internal operations playbook, I post it in Slack for feedback and accountability. It not only helps me feel more productive, but it also fosters a sense of friendly competition among my team.

Avoiding Negati...

25 Sep 2024 How To Hire For Growth 00:14:20

In this episode of Rogue Startups, I dug into several pressing questions from the community. From knowing when to pull the plug on a marketing channel to the debate around hiring for support versus sales, we covered ground that matters deeply to founders and entrepreneurs. Here’s a breakdown of the key takeaways that can help you level up your startup game.

Watch on YouTube

1. When Should You Know if a Channel is Working?

A common dilemma many founders face is determining whether a new marketing channel is working. If you’ve ever wondered how long you should invest in a channel before calling it quits, you’re not alone.

Here’s how I break it down:

  • Give New Channels at Least 90 Days: If you’re starting fresh with a channel, 90 days is the minimum timeframe to give it. Less than that is almost never enough.
  • Existing Channels Need Time Too: Even for established channels that you’re tweaking or optimizing, 90 days is still a good baseline. After that, look at the data to guide your decision.
  • Focus on Leading Indicators: Whether it’s impressions on LinkedIn, open rates in email campaigns, or early engagement in SEO, you need to assess the leading metrics first. These are the earliest signs that a channel is gaining traction.

For example, if you’re working on LinkedIn, impressions tell you whether your content is even being seen. Engagement and DM conversations are steps that follow, but focusing on what starts the funnel will help you decide if you should stick with it.

2. The Support, Success, or Sales Dilemma

Another big question I often get asked is, “How do I know whether I need to hire for support, sales, or customer success?” This decision depends largely on where your business is in its growth stage and the roles you want to fill.

  • Support Roles: These are typically more reactive—answering support tickets, maintaining a knowledge base, and troubleshooting. If customers are having common issues, or if onboarding is a bottleneck, it might be time to bring in a support team member.
  • Success Roles: Customer success is more proactive. The goal here is to ensure customers get the most value from your product. This role could be key if your customers are signing up but not converting to paid users, or if you’re looking to drive expansion revenue.
  • Sales Roles: Salespeople hunt for new business and close deals. If you’re looking to generate new demand or work with enterprise clients, this is the hire for you. Sales is more aggressive in its pursuit of growth, but if your inbound leads just need a quick demo, you may not need a dedicated salesperson—success could handle it.

I suggest founders think about these roles in terms of function and their contribution to revenue growth. Where is the biggest gap in your customer journey?

3. Focus on Customers and Revenue-Generating Activities

As entrepreneurs, it’s easy to get bogged down in tasks that feel productive but don’t directly drive growth. One of my favorite principles to live by is focusing on activities closest to your customers and revenue.

  • Direct Conversations Over Complex Funnels: Fancy marketing automation systems might feel like progress, but especially early on, nothing beats direct customer conversations. Whether it’s cold outreach or calling people in your network, it’s the quickest way to gather real data and refine your approach.
  • Avoid Procrastination vi...
09 Oct 2024 RS330: Product-Led Playbook with Wes Bush 00:47:52

Wes Bush is a leading authority on product-led growth (PLG) and is here to guide Craig through the playbook for implementing product-led strategies in your business. This episode is invaluable for entrepreneurs eager to understand how product-led growth works, as well as those skeptical about its effectiveness. Listeners will gain insights into the product-led mindset and methodology that Wes employs for successful PLG implementation.

Watch on YouTube

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights from Craig and Wes’ conversation:

  • Differences and Similarities Between Product-Led Growth (PLG) and Self-Service SaaS
  • How to Leverage PLG as a Marketing Tool
  • Internal to External Growth Loops (e.g., Canva)
  • Providing Value and Education to Empower Customers
  • Overcoming the Fear of Change and Embracing Creative Destruction
  • The Product-Led Implementation Program and Wes Bush’s New Book
  • From Contender to Leader: Navigating Your Market
  • Castos: A Case Study in Product-Led Growth

A Little About Wes:

Wes is an entrepreneur, author, and product-led coach. Over 500,000 people have read his Product-Led Growth book and listened to the ProductLed Podcast.

Links & Mentions from This Episode:

Wes on LinkedIn

Product-Led

“Why Nations Fail” by Daron Acemoglu and James A. Robinson

Rogue Startups Resources:

Follow Craig on Twitter/X

Craig on LinkedIn

Castos

Founder Insights

18 Dec 2024 RS331: I'm Still Here... 00:09:23

After a 2+ month hiatus, we're back! 

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Sorry for the pause in episodes, but thank you for tuning in this week. 

In this episode I talk through why the forever long break in the podcast, what I've learned in that time, and where things are with me and the business.

But most of all, I want to hear from you...what do you want out of this podcast.

Hit me up on Twitter, LinkedIn or even Bluesky

25 Dec 2024 RS332: Competing with Stripe and Hubspot (ft. Geoff Roberts) 00:39:14

Hey everyone! Just had an awesome chat with Geoff Roberts from Outseta (outseta.com). They're doing something pretty wild - basically smashing together Stripe and HubSpot into one platform for subscription businesses. How cool is that?

Quick Hits:
- Outseta is an all-in-one platform handling payments, auth, CRM, email, and help desk
- They've got this unique setup where everyone makes $210k/year (pro-rated) and can work 1-5 days a week
- Took them 4 years to really nail the product (hey, good things take time!)

Best Parts of the Convo:
- Jeff got real about marketing struggles (who hasn't been there?)
- Turns out ChatGPT is actually sending them customers now - wild!
- We had a great debate about whether SaaS is still the golden ticket (spoiler: it's way more competitive now)
- Talked about why sometimes it's better to stick with a "pretty good" business than chase the next unicorn

Where They're Headed:
- Aiming for $10M in revenue with a lean team of about 20 people
- Shifting from being super product-focused to really pushing growth
- Geoff's been at it for 8 years and plans to keep going for 7 more

Real talk: This episode is perfect if you're building a SaaS company or thinking about bundling multiple tools together. Geoff drops some serious knowledge about what it's actually like in the trenches.

Check them out at outseta.com if you want to see what they're building!

#SaaS #Startups #Entrepreneurship

01 Jan 2025 RS333: Grading My Business (and yours!) 00:22:03

In this New Year's Eve 2024 episode, we dive into a framework for evaluating SaaS businesses across eight crucial criteria. Instead of doing a typical year-in-review or making predictions, we explore how to assess the fundamental strength and potential of your business.

Episode Highlights

Craig grades Castos (podcast hosting platform) across eight key criteria for evaluating SaaS businesses:

1. Pricing (6/10)
- Core product (podcast hosting) averages $28/month - below ideal $50+ threshold
- Production services start at $1,500/month
- Enterprise clients pay tens of thousands annually
- Mixed pricing model affects overall score

2. Churn (9/10)
- Extremely low churn rate
- Attributes success to:
- WordPress integration
- Premium pricing (no free tier)
- Strong technical reliability

3. Payment Processing Integration (4/10)
- Offers multiple monetization options:
- Castos Ads
- Castos Commerce
- Donations
- Paid subscriptions
- Private podcasting
- Limited adoption of direct monetization features
- Most customers monetize indirectly through business growth

4. Switching Costs (6/10)
- Technically easy to switch providers
- High retention due to ongoing necessity
- Perceived switching cost higher than actual

5. Technical Advantages
- WordPress integration provides unique value
- Core functionality similar to competitors
- Important lesson: Customer needs often simpler than assumed

6. Expansion Revenue (3/10)
- Limited expansion opportunities
- Most customers stay at $19/month
- Working to add upgrade opportunities
- Identified as major growth limitation

7. Established Market Need (10/10)
- Clear market position
- Well-understood service category
- Strong product-market fit

8. Customer Acquisition (6/10)
- Success with content marketing, SEO, partnerships
- Struggling with paid acquisition
- Limited by low price point
- Working on improving paid channels

Key Takeaways

- Overall Business Grade: B (maybe 80/100)
- Growth Ceiling: Business could potentially double but unlikely to become a $50M/year company
- Main Limitations:
- Low initial price point ($19/month for most customers)
- Limited expansion revenue
- Restricted marketing channels due to unit economics

Looking Forward

Future episodes will mix personal insights about founding and running a business with interviews featuring successful founders.

08 Jan 2025 RS334: How AI Saves Me 10 Hours A Week 00:15:51

Today, I’m kicking off a series on AI—how I’m using it personally and professionally to grow my business, make life easier, and operate at a higher level.

Over the next few episodes, I’ll be chatting with folks about the real ways they’re using AI in their businesses. If you’re interested in joining the conversation, hit me up (details below). But for now, here’s a breakdown of how I’m incorporating AI into my own work.


Key Ways I’m Using AI in My Business

  1. Content Creation for Programmatic SEO

    • Using OpenAI and Claude to create use case pages for Castos.
    • Built a process to programmatically generate 100+ SEO landing pages using Google Sheets and templates.
    • Example use case: Why Startups Should Start a Podcast for Thought Leadership.
  2. Custom GPT for YouTube Scripts

    • Created a custom GPT workflow to script our Castos YouTube videos.
    • Process: Provide a topic, feed it examples, and let GPT draft outlines and scripts.
    • Outcome: High-performing, 90%-ready scripts I tweak and personalize.
  3. Building Free Marketing Tools

    • Leveraging tools like Replit and Cursor to develop free tools for Castos (e.g., podcast name generator, social post creator).
    • Focus: Engineering as marketing to drive traffic and lead generation.
  4. Documenting Internal Processes

    • Using Loom to record workflows (e.g., triaging support tickets).
    • Leveraging AI to convert videos into detailed step-by-step process documentation (aka playbooks).
  5. Automating Low-Level Tasks (Future Plans)

    • Exploring tools like Make and Airtable for automating repetitive processes (e.g., email tagging, Slack notifications).
    • Goal: Free up mental energy for high-value activities like sales, marketing, and strategy.

Takeaways and Vision

AI is transforming the way we work, and I’m all in on finding ways to integrate it into every aspect of my business. It’s not just about saving time; it’s about leveling up and creating systems that make the impossible possible.

I’m inspired by the idea of building something like an 8-person, $10M business with AI at its core. That’s where I’m headed—and I want to bring you along.


Resources and Links from This Episode


Want to Share Your AI Story?

I’m looking for guests to share how they’re using AI in their businesses. If you’ve got some great examples or unique insights, reach out to me:

Let’s level up together!

22 Jan 2025 RS335: Evaluating AI Model Performance with Stuart Grey 00:47:06

In today’s episode of Rogue Startups, Craig sits down with AI expert Dr. Stuart Grey to discuss how AI is transforming both his personal and professional life. Dr. Grey also shares how he educates his students and clients on AI applications. He believes AI will play a pivotal role in all of our futures, and while there may be hesitations, AI can be harnessed to create high-quality content and drive innovation.

 

Watch on YouTube

Over the next few episodes, I’ll be chatting with folks about the real ways they’re using AI in their businesses. If you’re interested in joining the conversation, hit me up (details below). But for now, here’s a breakdown of how I’m incorporating AI into my own work.

Highlights from Craig and Stuart’s conversation:

  • What it’s like to teach AI and machine learning at the university level
  • Comparing AI prompts across different platforms and analyzing results
  • Stuart’s AI Rules of Thumb for efficient content generation
  • Ethical considerations when using AI technologies
  • A glimpse into the near future of AI in everyday life and business
  • The two primary types of AI-driven content creation
  • How to turn basic AI-generated content into exceptional material

Takeaways and Vision

AI is integrating into our daily lives and everyone needs to learn how to leverage this powerful technology to save time and enhance productivity. Whether you’re just starting or an established professional, understanding how to work alongside AI-powered tools is key to staying ahead in your career.

Resources and Links from This Episode

Want to Share Your AI Story?

I’m looking for guests to share how they’re using AI in their businesses. If you’ve got some great examples or unique insights, reach out to me:

29 Jan 2025 RS336: Claude Project Deep Dive with Alison French 00:47:43

On today’s episode of Rogue Startups, Craig continues his AI series with founder, marketer, and Claude-user Alison French. They discuss the hesitation creators feel when working alongside AI and what Alison did to overcome that hurdle. Since then, she’s taught herself how to use Claude.ai in her creative and professional work. AI is a tool that everyone has to learn how to use. 

Watch on YouTube

If you feel our podcast has benefited you and might benefit someone else, please share it with them. Also, if you have a chance, please give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights from Craig and Alison’s conversation:

  1. How creatives can use AI to improve their professional and personal lives
  2. How to fine-tune Claude’s tone of voice:
  • Add files to the specific project only
    • You have to feed the machine with information that matters
    • Over time, working within the same project, Claude will tune itself to your prompts
How to have Claude see references and change the tone or voice
  • Separate and break down transcripts by prompt to hone in on specifics
Claude is like a junior copywriter: work with it and nurture it, and it will help your work go faster so you can focus on the important things. Craig’s creative process when creating content:
  • Get examples/models, templates, and ideas to input into your AI program of choice.
  • Break your content up into different functions. Go in once a week to pull out topics.
Put the time and energy into refining one meaty piece of content that you can use over and over again.
  • You have to focus on what makes you credible to your audience
How does your team embrace and respond to AI because at the surface it’s a risk for all of us?
  • How do we educate our youth now, for a future with AI?

Takeaways and Vision

Balancing the importance of human connection with the ability to express your individuality and be yourself is even more possible in this AI era. Adopting and embracing technology and AI in your personal and professional lives can help save you time and free up some creative energy for being social, innovative, and expressing yourself. AI will give you the time to do the work to open yourself up to having personal experiences.

Resources and Links from This Episode

 

05 Feb 2025 RS337: Building AI Native SaaS w/ Jordan Gal 00:48:06

Today, Craig chats with Jordan Gal from Rosie about starting a business centered solely on AI. While many of us use AI to help with our work tasks and streamline certain jobs, Jordan’s whole business is AI. They discuss how you and your customers can use AI, what it’s like to start a company right now, and what AI is doing to SaaS.

Rosie creates a new option for small businesses. Previously, the only way to handle phone calls during work hours was through voicemail or an answering service. Rosie offers a new option in that market: an AI can answer the phone for you and handle the tasks needed for these calls, whether it’s taking messages, sending messages out, or talking to clients.

Highlights from Craig and Jordan’s conversation:

  • Non-technical CEOs sympathize more with customers
    • Jordan views his engineering company as customers see their product
    • Because of this, he knows how Rosie helps businesses run better
  • Using AI to help the customer understand their data vs building a product that was not possible before AI
  • Create milestones for the team when creating a brand-new product
    • Jordan tells his team to work as if they are onboarding 100 customers a day
  • Dealing with customers that have different knowledge bases of your type of product
    • Remove marketing fluff to speak plainly to possible customers
    • If you provide the customer with something they truly need and get value from, they will find ways to deal with those roadblocks
  • Conversion versus usage numbers: how to avoid churn
    • Freemium and usage-based trials
  • What AI has done to SEO: people are led to video and YouTube
  • Software in the AI era
    • Now is a good time to bootstrap; it is not a good time to raise money
  • Everything you do has to have leverage

Takeaways and Vision:

Everything in technology is time-sensitive because tech improves and evolves so fast. Rosie shows us that AI can do much more than just answer questions, run some numbers, and analyze data. Whether you’re using AI to help your business run better, or if you’re creating the next AI tool, now is the time to embrace this technology.

Resources and Links from This Episode:

 

26 Feb 2025 RS338: Balancing Your Use of AI with Aaron Francis 00:52:12

Ever wonder what's happening behind the scenes when your dev team says they're "leveraging AI"? As a non-technical founder, you don't need to understand every line of code, but knowing how AI is actually being used in your business is becoming essential.

Today I'm sitting down with Aaron Francis, who pulls back the curtain on AI in development work. We'll explore the surprising differences between how veterans and newcomers in the field are using these tools, the common pitfalls teams fall into, and the unexpected ways AI is transforming how products get built. Whether you're trying to speak your developer's language or just want to ensure your company is using AI effectively, this conversation will give you the insights you need.

 

Highlights from this Episode:

  • Are junior developers utilizing AI too much?
  • Creating a balance between overusing AI and being a Luddite
  • How Aaron uses Claude for “discrete” tasks
  • Developers aren’t going away anytime soon
  • Balancing the use of AI without depending too much on it
  • Harnessing the power of AI for your business
  • AI tools are both calming and scary for founders
  • Aaron’s different uses for 01 Pro
  • What AI can do versus what AI should do and undeniably human tasks
  • Where to go to educate yourself about AI
  • The importance of testing and checking AI work

 

Resources and Links from this Episode:

  • Try Hard Studios: https://tryhardstudios.com/
  • Aaron Francis: https://x.com/aarondfrancis
  • Reforge: https://www.reforge.com/profiles/brian-balfour
  • SWYX: https://x.com/swyx
  • https://www.youtube.com/@JeffSu
  • https://www.youtube.com/@SkillLeapAI
  • https://www.youtube.com/@MATGpod
  • Email me: podcast@roguestartups.com
  • Find me on Twitter:  https://twitter.com/TheCraigHewitt
05 Mar 2025 RS339: AI Skeptic, or Believer 00:47:49

In today’s episode, Craig chats with Anthony Eden from DNSimple about how they use AI in their businesses and their personal lives. As early skeptics of AI, they do a deep dive into what made them change their minds, what AI does for them, and how it might actually be holding people back. Like the internet, AI is a powerful tool people can use to make their lives better. 

They also chat about what it’s like to raise kids as entrepreneurs. Has their influence improved or hindered their children’s lives? Not to mention, how do they balance their work life and personal life and is AI helping them with that balance?

Anthony Eden is the creator and founder of DNSimple. He has been developing web applications since the early days of the web (1995) using Ruby, Erlang, Golang, and other languages. He used to publish a podcast called the Strong Businesses Podcast with Steven Bristol. He also published a mostly weekly podcast of progressive dance music over at theministerprime.com. He also produces tracks which can be found on SoundCloud.

Highlights from Craig and Anthony’s conversation:

  • What changed Anthony and Craig’s minds about AI
  • How to, as an entrepreneur, leverage AI without just “chasing the trend”
  • The personal and emotional impacts of running a business in this AI world
  • What AI will do for the future of business and SaaS
  • Training AI and what the “mistakes” teach you and your team
  • “I have to have a little bit of fear in everything I do [as a founder].”
  • Keeping customer data safe and secure
  • What data is AI using to aid you with your business?
  • “This kind of stuff is fantastic but, boy, does it make you lazy.”
  • As an entrepreneur, how do you talk to your kids about careers after college?
  • How is generative AI going to make our lives better?

Takeaways and Vision:

How do you take a non-native AI solution and adapt it to a solution for your customers, your team, and your business? As a founder and entrepreneur, how you use AI in your business is important. Not only do you have to pay attention to what information you are getting from AI, but how it is affecting your productivity overall. 

Resources and Links from This Episode:

19 Mar 2025 RS340: Is AI Killing SaaS w/ Tim Schumacher 00:43:00

In this episode of Rogue Startups, Craig sits down with founder and entrepreneur Tim Schumacher to discuss his insights on AI, the future of SaaS, and what makes a company successful.

In 2001, Tim co-founded Sedo.com, the world's largest domain marketplace. Since selling the company, he’s been active as an Entrepreneur and/or Investor in various start-ups, such as Eyeo (makers of Adblock Plus), Ecosia, Hitfox, Aklamio, Miomente, PiwikPro, BasicThinking, Home, Zolar, Joblift, SaaS.group, and others. 

Highlights from Craig and Tim’s conversation:

  • The future of SaaS keeps founders up at night
  • Using artificial intelligence to analyze feedback and company metrics for smarter decision-making
  • How to make your data, and your customers' data, available across multiple platforms and environments
  • What impact will AI and automation have on the economy and the future of work?
  • Why are some in the SaaS industry still hesitant to adopt AI, and what are their fears?
  • Key factors that drive business growth and longevity.
  • Product-Market Fit vs Founder-Market Fit: Understanding the difference and why both matter.
  • Starting a business at the intersection between climate tech and AI
  • Remote work vs in-office culture: How the workplace dynamic is evolving in the age of digital transformation.

Resources and Links Mention in This Episode:

If you feel like Rogue Startups has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. Do you have any comments, questions, or topic ideas for future episodes? Feel free to reach out to me:

26 Mar 2025 RS341: Microconf 2025 Recap 00:17:48

Craig recaps his biggest takeaways from MicroConf 2025, reflecting on lessons in positioning, lead generation, conference ROI, and the power of going all in on what’s working. From tactical marketing insights to personal reflections, this episode delivers both strategic clarity and founder fuel.

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