Moving Beyond Task Automation to Build Around Outcomes with Sam Kroonenburg

Past success can become a liability when it convinces you that the way you built before is the way you should build next.

Sam Kroonenburg knows what it feels like to build at scale. He co-founded A Cloud Guru, helped grow it into a business serving millions of learners, and eventually sold the company to Pluralsight. Now, as CEO and co-founder of Cuttable, he’s back at the beginning: finding customers, testing assumptions, shipping imperfect products, and learning how different company-building looks in the AI era.

In our conversation, we explore what Sam had to unlearn when he moved from running a 600-person company back into an early-stage startup. We get into why Cuttable walked away from nearly $1 million in annual recurring revenue, how enterprise customers can pull a young company away from the product it actually needs to build, and why AI is shifting product and engineering teams from owning parts of a system to owning measurable outcomes.

• Past success can distort your judgment: Starting Cuttable reminded Sam that reputation means little if the product does not solve a problem customers will pay for.
• Experience does not transfer automatically: Sam could trust his instincts when building for engineers, but entering advertising required him to test assumptions and learn from customers.
• Revenue can hide the wrong product: Cuttable reached nearly $1 million in ARR while engineers were still manually doing work the product was supposed to automate.
• Taking the long view can require a reset: Sam and his co-founders released every customer, returned to zero revenue, and rebuilt around end-to-end automation.
• AI shifts the focus from tasks to outcomes: Instead of teaching AI to copy a human process, teams should define the desired result and let AI determine how to achieve it.

• Speed can be an advantage over scale: A Cloud Guru prepared courses before AWS certifications launched, then updated them using real exam feedback.
• Playfulness can strengthen a product: Short, entertaining lessons made cloud training easier to engage with and helped A Cloud Guru stand out.
• Paying customers provide stronger signals: Payment shows whether a problem matters enough to solve and makes the customer’s feedback more meaningful.
• AI is changing team ownership: Cuttable is moving from teams that own system components to teams accountable for measurable customer outcomes.
• Founder optimism needs a counterweight: Glitch Capital uses analysts and experienced operators to challenge assumptions and add rigor to investment decisions.

00:00 – Episode Recap

Sam reflects on starting again after a major exit and learning that customers care more about solving their problem than a founder’s reputation.

02:13 – Guest Introduction: Sam Kroonenburg

Meet Sam Kroonenburg, CEO and co-founder of Cuttable, co-founder of A Cloud Guru, and founder investor at Glitch Capital.

03:29 – The Moment Technology Clicked

Sam traces his entrepreneurial journey back to receiving his first computer and learning to code through an online pen pal.

09:11 – Winning Through Speed and Play

Sam explains how A Cloud Guru used informed bets, rapid updates, and playful learning experiences to move faster than larger organizations.

12:26 – Starting Again and Unlearning Founder Instinct

Moving from a 600-person company to an early-stage startup forced Sam to test his assumptions and relearn how to earn customer trust.

17:51 – Running a Startup Like a Large Company

Sam initially brought too much structure, reporting, and sales pressure into Cuttable before refocusing on product-market fit.

20:56 – Why Cuttable Went Back to Zero

After reaching nearly $1 million in ARR, Cuttable released every customer and rebuilt around end-to-end automation.

27:48 – Why Paying Customers Change the Signal

Sam explains why payment reveals whether a problem matters enough to solve and makes customer feedback more meaningful.

29:43 – Stop Teaching AI to Work Like a Human

Cuttable learned to give AI the available data and desired outcome instead of forcing it to follow a prescribed human process.

34:45 – Organizing Teams Around Outcomes

Sam explores why engineers focused on customer impact often embrace AI and how Cuttable is organizing teams around measurable outcomes.

38:41 – Why Founder Optimism Needs a Filter

Sam explains how Glitch Capital balances founder optimism with analysts and experienced operators who challenge assumptions.

42:03 – Smaller Teams and Bigger Impact

Sam shares his optimism that AI will help smaller teams create impact at a scale that once required much larger organizations.

Sam had to unlearn the confidence and operating habits that came with previous success. At Cuttable, he found that reputation could not replace customer value, evidence, or the search for product-market fit.

Enterprise demands were pulling Cuttable toward custom work and manual intervention. When engineers began generating and fixing campaigns themselves, the team released those customers and rebuilt around end-to-end automation.

Sam believes teams should spend less time telling AI how to perform a task and more time defining the desired outcome. AI can then use the available data to determine the best method.

Payment shows that a problem matters enough to solve. Free users can offer feedback without genuinely valuing the product, while paying customers provide a stronger signal.

Cuttable is organizing teams around measurable customer outcomes instead of software components. Teams can use AI and evaluation systems to improve those outcomes continuously.

• Cuttable — Sam Kroonenburg’s AI-powered creative production system for advertising.
• A Cloud Guru — The cloud computing education company co-founded by Sam and later acquired by Pluralsight.
• Glitch Capital — The Australia and New Zealand founders fund Sam started with fellow founders and operators.
• AWS re:Invent — Discussed in Sam’s story about how A Cloud Guru prepared training for new AWS certifications at launch speed.
• Square Peg — Cuttable’s investor, whose response to the company’s decision to reset revenue reinforced Sam’s understanding of seed-stage investing.
• Artificial Organizations — https://geni.us/artificialorgs
• Read Artificial Organizations? Leave a review on Amazon - https://www.amazon.com/review/create-review/ref=cm_cr_othr_d_wr_but_top?ie=UTF8&channel=glance-detail&asin=1067626328

LinkedIn: https://www.linkedin.com/in/barryoreilly

Website: https://barryoreilly.com

Facebook: https://www.facebook.com/barryoreillyauthor/

X: https://x.com/barryoreilly

Instagram: https://www.instagram.com/barryoreilly/