Rogue Startups

While we weren’t looking, AI has quietly embedded itself into the coaching world. Today Craig sits down with new cohost Colin Gray, founder of Alitu and The Podcast Host, to unpack the current state of the industry.

They dig into why coaching is shifting from information delivery to accountability and thinking-partner work, how Colin built an AI system using Granola transcripts to track patterns across coaching clients and surface his own best ideas for content, and whether "everyone is a media company" still holds up for B2B, legal, and SaaS businesses that swear they're different. 

It's a candid, practical conversation about personal brand versus business brand, one-on-one versus group coaching, and using tools like Claude not to get answers but to get better questions - a must-listen for coaches, consultants, and any solo founder trying to figure out where human expertise still beats a chatbot. 

Highlights from Craig and Colin’s conversation:

AI can't coach you. It can only answer you.

The "how-to" business is dying, and courses are the first casualty.

Why one podcaster treats Claude like a co-founder (and where that backfires).

Coach or mentor? The real spectrum nobody talks about.

Selling a podcast editing app for millions, then figuring out what's next.

"Personal brand" is a dirty word. Here's the better way to think about it.

The one B2B industry everyone assumes content can't touch (it can).

Coaching's new job: not answers, accountability.

One-on-one vs. group coaching: which one actually makes people feel heard.

Turning client call transcripts into an AI memory system that spots patterns humans miss.

Mining your own coaching sessions to find your most original ideas.

Resources and Links from This Episode:

Produced by Castos Productions 

The Podcast Host: https://www.thepodcasthost.com/ 

Colin on LinkedIn: linkedin.com/in/colinmcgray?originalSubdomain=uk 

Castos Free Tools: castos.com/tools

Email me: podcast@roguestartups.com 

Find me on Twitter: https://twitter.com/TheCraigHewitt 

LinkedIn: https://www.linkedin.com/in/craig-hewitt-78386a66/  

Email: podcast@roguestartups.com

Chapters

(00:00:00) - A Coach's Role in Your Business
(00:00:32) - Colin Gray Training for His First Half Marathon
(00:02:35) - Meet Alitu
(00:04:55) - Craig on His Exit
(00:05:28) - Interviewing Silicon Valley's Rich People
(00:05:57) - AI for Coaching and Business
(00:09:38) - What Kind of Coaches Should You Work With?
(00:11:35) - How to grow a creator business in 2019
(00:13:31) - Are Businesses Ready to Be a Media Company?
(00:16:01) - Podcasting: The Best Use Case for Content
(00:16:40) - Colin Gray on His Personal Brand
(00:19:29) - Group Coaching vs One-on-One
(00:23:30) - How AI is helping me with my coaching
(00:28:07) - The AI Product Hype Cycle

What happens when AI changes the rules of building a software company? According to Jason Cohen, the answer isn't to predict the future. It's to build around things that remain valuable no matter how technology changes.

In this episode of Rogue Startups, Craig Hewitt talks with Jason Cohen, founder of WP Engine and SmartBear and author of Hidden Multipliers, about growth, strategy, positioning, and building durable businesses in an age of AI. Jason explains why founders should focus on the transformation customers actually want instead of simply adding AI to their products, why repositioning a product can dramatically increase its value, and how to identify the special combination of strengths, customers, and opportunities where your business can win.

Craig and Jason also dig into what kinds of jobs AI is likely to replace, why human creativity and personality remain incredibly valuable, how Jason develops the ideas behind his writing, and why copying someone else's successful framework rarely works without adapting it to your own company culture.

Whether you're building a bootstrapped SaaS company, leading a growing startup, or trying to figure out where your business fits in an AI-driven world, this conversation is full of practical ways to think more clearly about strategy, growth, and competitive advantage.

Highlights from Craig and Jason’s conversation:

How to make strategic decisions in an uncertain market

What customers will still value in the age of AI

Why AI should solve customer problems rather than simply be added to products

How positioning can dramatically increase a product's value

Why senior developers benefit more from AI than junior developers

What chess teaches us about AI and human creativity

Why human personalities still matter in content and marketing

How Jason Cohen developed the ideas behind Hidden Multipliers

Why copying successful business frameworks often fails

How founders can find their own strategic advantage

The right and wrong ways to use metrics

What AI means for the future of SaaS

Resources and Links from This Episode:

AI Skills which facilitate ideas from the book and Jason’s articles

https://longform.asmartbear.com/

Jason on X: https://x.com/asmartbear

hiddenmultipliers.com 

Castos Free Tools: castos.com/tools

Email me: podcast@roguestartups.com 

Find me on X: https://twitter.com/TheCraigHewitt

Craig on LinkedIn: https://www.linkedin.com/in/craig-hewitt-78386a66/  

Chapters

(00:00:00) - Will Jobs Get Automated?
(00:00:37) - Interviewing Jason Cohen on Growth
(00:01:41) - The Making of the Smart Beer Live Podcast
(00:06:48) - How to Figure Out the Most Important Things in the Business
(00:10:15) - Re-positioning Your Business Software
(00:11:45) - Costs of AdWords and AI
(00:17:23) - "I Never Want to Watch a Computer"
(00:20:16) - Behind the Hidden multipliers: How to Grow a Business
(00:24:00) - Your Thoughts on Writing
(00:29:51) - Reasons for a Startup Framework Fit
(00:34:09) - The Common Truth of Metrics
(00:37:18) - Do You Need Metrics in Your Company?
(00:40:35) - Top 5 Things AI Will Affect in 2030
(00:45:22) - Do Jobs Get Replaced by AI?
(00:47:25) - No Unique Advantage?
(00:49:51) - Book Review

Selling a business isn't just about timing the market. It's about knowing yourself.

In this episode of Rogue Startups, Craig Hewitt sits down with Colin Gray, founder of Alitu and The Podcast Host, to discuss what it's really like to sell a SaaS company after 15 years. Colin shares why he decided to exit, how founders should think about timing a sale, the emotional side of letting go of a business, and why "stair-stepping" through multiple businesses may be a smarter path than chasing a single life-changing exit. They also explore how AI is reshaping SaaS, content marketing, and YouTube, as well as what comes next after selling a company you've spent years building.

Whether you're thinking about selling a business someday or simply trying to build one that lasts, this conversation is packed with honest advice from two experienced bootstrapped founders.

Highlights from Craig and Colin’s conversation:

How to know when it's time to sell your business

The stair-step approach to building wealth

Founder burnout and losing passion for your company

The realities of SaaS valuations today

Why building an audience before software matters

AI's impact on SaaS and content marketing

Why YouTube is still one of the best marketing platforms

Life after selling a startup

Bootstrapping vs. venture-backed growth

Lessons from two experienced SaaS founders

Resources and Links from This Episode

The Podcast Host: https://www.thepodcasthost.com/ 

Colin on LinkedIn: linkedin.com/in/colinmcgray?originalSubdomain=uk 

Castos Free Tools: castos.com/tools

Email me: podcast@roguestartups.com

Find me on Twitter: @TheCraigHewitt 

Twitter: @TheCraigHewitt 

LinkedIn: Craig Hewitt 

Email: podcast@roguestartups.com

Chapters

(00:00:00) - How to Get Out of Debt in Retirement
(00:01:33) - A Chat With Colin on Rogue Startups
(00:02:54) - When Should You Sell Your Business?
(00:09:18) - Ideas for Buying or Selling Our Company
(00:14:57) - Allevi On Falling Out Of Love With the Business
(00:16:56) - How to Balance Working and Living
(00:21:12) - Getting a Job in the Age of AI
(00:23:01) - Ex-CEO on His Exit
(00:27:08) - Podcasting: The SaaS Jobs Apocalypse
(00:29:23) - SaaS and Content: The Future of Both
(00:36:43) - How to Keep Your YouTube Channel Updated
(00:39:47) - Under Threat: Podcasts and Video
(00:41:21) - Alitu Expands Into Paid Acquisitions
(00:43:26) - Exclusives: Colin's Exit
(00:44:29) - Co-Hosting: Solo or Team?

If you're building a SaaS company, one of the hardest questions you'll face isn't how to build a product. It's what to build next.

In this episode of Rogue Startups, Craig Hewitt talks with Steve McLeod, founder of Feature Upvote and author of Kill the Hippo, about product strategy, customer research, and why the loudest customer isn't always the one you should listen to. Steve shares lessons from interviewing successful bootstrapped SaaS founders, explains why talking directly with customers beats relying on surveys and feature voting alone, and discusses how companies can avoid building the wrong features.

Craig and Steve also explore Steve's journey writing Kill the Hippo, Feature Upvote's successful pivot into the gaming industry, the realities of running a mature SaaS business, and how AI is changing product development and customer acquisition. They close with an honest conversation about the future of bootstrapped SaaS and why today's founders face a very different landscape than they did just a decade ago.

Whether you're launching your first startup or leading an established software company, this episode is full of practical advice on product management, customer feedback, ideal customer profiles (ICP), founder decision-making, and sustainable SaaS growth.

In this episode: 

00:00 Why Building the Right Product Matters

01:43 Why Steve Wrote Kill the Hippo

03:09 The Pivot That Changed Feature Upvote

04:36 Why the Most Popular Feature Is Usually Wrong

06:26 Talk to Customers, Not Just Surveys

08:19 Finding Your Real Ideal Customer

13:05 How Kill the Hippo Came Together

16:59 Why Steve Wanted to Write a Book

19:04 The Reality of Being a Solo Founder

21:06 Are Product Prioritization Frameworks Worth It?

23:54 Hiring People Who Think Like Your Customers

27:45 Building for Future Customers Without Losing Today's

29:24 Product Strategy for Mature SaaS Companies

31:26 Avoiding the "Abandoned Product" Trap

34:00 How Mature SaaS Teams Ship New Features

36:19 Build Features That Make Customers Say "Wow"

38:20 Is SaaS Really Dead?

42:35 The Golden Age of Bootstrapped SaaS

Resources and Links:

- Feature Upvote: https://featureupvote.com/  

- Steve on LinkedIn: https://www.linkedin.com/in/steve-mcleod-fuv/ 

- Castos Free Tools: castos.com/tools

- Email me: podcast@roguestartups.com 

- Find me on Twitter: @TheCraigHewitt

- Craig on LinkedIn: http://linkedin.com/in/craig-hewitt-78386a66  

If you feel Rogue Startups has benefited you and might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. 

Chapters

(00:00:00) - Knowing What Product to Build in the SaaS Age
(00:01:45) - Writing a Book About Pivoting
(00:04:14) - How to Decide What to Build Next
(00:10:27) - Have You Changed Your ICP?
(00:12:37) - Writing The Bootstrap Book
(00:16:26) - What are you hoping the book does for you?
(00:18:08) - In the Elevator With a Co-founder
(00:23:10) - The Importance of Talking to Customers
(00:27:54) - How Do You Keep Your Product From Getting Stuck?
(00:30:04) - A Design for Less Annoying CRM
(00:32:24) - How To Evolve a Matured Product
(00:34:47) - The Need for a 'Wow'
(00:36:25) - SaaS and the future of podcast
(00:40:56) - Bootstrapped SaaS: The Golden Age is Over
(00:42:40) - Kill the Hippo

After an almost 5 month break from the podcast, I'm Back!

In this episode I talk through updates with me, Castos, my coaching business, and where the podcast is headed into the future. Spoiler alert...i'm getting a new cohost.

Connect on the socials:

x.com/thecraighewitt

instagram.com/thecraighewitt

https://www.linkedin.com/in/craig-hewitt-78386a66/

Chapters

(00:00:00) - Rogue Startups: A Year in the Life
(00:00:45) - Q&A: The Future of Podcasting
(00:06:10) - Coaching Isn't Dead
(00:10:01) - What Would You Do If You Could Do Whatever You Want To Do