This week, Dan picks up with Alexis Sikorsky—entrepreneur, investor, and founder of Knight Scale Partners—for the tactical follow-through: what great private equity actually brings, how to replace yourself post-acquisition ("please chairman me"), why agility beats prediction in a world of Black Swans/"Black Dragons," and how agencies can still win as AI re-sorts the field. If you're navigating uncertainty, planning pivots, or gearing up for an exit, this continuation is packed with clear plays and hard-won context.

Show Highlights

• What great PE actually brings: cost discipline, better people, and world-class sales—why the dream target has a weak or no sales team. [00:00:49]
• "Please chairman me"—why Alexis replaced himself as CEO and why being chairman can be the best job in the world. [00:02:07]
• Exit math that stuns: sold remaining shares for an undisclosed nine figures; two years later buyers resold for +60%, ~16× cash multiple. [00:02:36] [00:03:03]
• Retired, then Oxford: why he went back to school, started advising (even pro bono), and turned mistakes into a playbook. [00:03:52]
• Two superpowers: leadership (not management) and turning complexity into five actionable steps. [00:06:44]
• Triple headwind case study: clients dying, business model dying, channel dying—plus "Google is in panic." [00:11:06]
• Pivot playbook: keep your domain (e.g., real estate), expand geographies, diversify inbound (podcasts/LinkedIn), and add warm outbound. [00:13:28] [00:14:41]
• AI won't erase agencies—it will empower fewer winners (think 6,000 → 600); VCs shifting to AI-enabled efficiency. [00:15:28]
• Black Swans ("Black Dragons"): don't time them—build agility and expect a crisis about every decade; a leveraged-forex cautionary tale. [00:17:36] [00:18:38]
• War-chest rule: keep ~9 months of burn so shocks don't kill you. [00:20:14]
• Sci-fi as systems training: Asimov and a love letter to The Three-Body Problem (especially the brutal Book 3). [00:21:58] [00:23:33]
• Cashing Out: a simple method to go from small to less small—and how to speak private equity. [00:24:54]
• Where to find him: Knight Scale Partners (with a K), LinkedIn, and Instagram—unique name makes him easy to find. [00:26:56]

For more updates and my weekly newsletter, hop over to https://betterquestions.co/

To learn more about Alexis Sikorsky, check out the websites below:

https://www.knightscalepartners.com/

https://www.linkedin.com/in/alexis-sikorsky-consulting/?originalSubdomain=uk

This week, Dan sits down with Alexis Sikorsky, founder of Knight Scale Partners, to unpack how to build, transform, and exit companies the smart way. Alexis shares the strategy behind "moving like a knight," a crisp 3–4 year planning window with one-month reaction time, the metrics he watches, and the story behind selling his banking software company, why he took 85% cash / 15% earn-out, and how the earn-out ended up paying more. If you want a practical playbook for scaling value without losing your mind (or your house during a crisis), this is it.

• Why the knight? Strategy behind Knight Scale Partners—anticipate, "play with the whites," and win by moving differently. [00:03:02]
  
  

• The planning horizon that actually works: 3–4 years…with a one-month reaction time for pivots. [00:06:12]
  
  

• What to measure: start with TAM, then track LTV/CAC monthly—keep the dashboard simple. [00:11:05]
  
  

• Start with the founder's goal: the surprisingly universal number is $40M and why. [00:17:23] (derived from the transcript section referencing "40 million")
  
  

• 2008 hits: lost 75% of revenue in a day—and the seven-year grind back. [00:26:23]
  
  

• The deal that changed everything: 85% cash / 15% earn-out up front… [00:30:44]
  
  

• …and why the earn-out paid more than the cash. [00:31:10]
  
  

• What great PE actually brings: cost discipline and world-class sales; why "no sales team" is a PE dream. [00:32:02]
  
  

• Alexis' two superpowers: leadership and turning complexity into five actionable steps. [00:56:27]
  
  

• "Black Dragons" (a.k.a. Black Swans): build 9 months of war chest and design for agility. [00:49:56]
  
  

• What Alexis reads for complex thinking: The Three-Body Problem (and The Dark Forest). [00:56:49]
  
  

• Cashing Out: Alexis' simple method to go from ~$10M to $100M valuation; audiobook now available. [00:56:58]
  
  

• The Virtual C-Suite: fractional, high-caliber execs as an unfair advantage; early traction & LTV/CAC math. [01:07:03]

For more updates and my weekly newsletter, hop over to https://betterquestions.co/

To learn more about Alexis Sikorsky, check out the websites below:

https://www.knightscalepartners.com/

https://www.linkedin.com/in/alexis-sikorsky-consulting/?originalSubdomain=uk

This week, Dan picks up right where he left off with Jason Yeh, founder of Scaling Freedom, for a rapid-fire dive into the real-world side of AI. Jason shares battle-tested frameworks for deciding when to use AI (and when a simple script is smarter), explains why human connection will matter even more as automation spreads, and gets personal about parenting, education, and staying nimble in a market that changes every week. If you're wondering how to weave clarity, technology, and meaning together—without losing the human spark—this conversation is for you.

• Treat AI like a smart "drunk intern"—speak out loud, let it interview you, and watch the prompts improve [00:00:31]

• Build a custom GPT that turns raw thoughts into perfectly engineered prompts [00:02:37]

• "AI on a bad system just scales the mess"—why process always comes before tooling [00:04:36]
  
  

• The hidden gold mine of manual data entry and how scraping invoices unlocks insights [00:06:51]

• Jason's 4-point litmus test for any AI project: Painful · Existing process · High impact · Strong data [00:09:56]

• Planner vs. Solver: use one "conductor" agent plus narrow specialists for higher accuracy [00:17:13]

• Klarna's chatbot fiasco & the lesson: some moments demand a human, not a bot [00:18:28]

• "Connection is the new currency"—brands that stay human will win customer loyalty [00:23:09]

• Staying nimble: why Jason refuses to ossify into a single product in a hype-driven market [00:24:45]

• The next frontier: AI-personalized education and raising kids who still think critically [00:28:12]

• Using Perplexity for curiosity walks and co-creating bedtime stories with your kids [00:32:37]

For more updates and my weekly newsletter, hop over to https://betterquestions.co/

To learn more about Jason Yeh, check out the websites below:

https://scalingfreedom.ai/

https://www.linkedin.com/in/jasonjyeh/

This week, Dan sits down with Jason Yeh, founder of Scaling Freedom, to talk about identity, resilience, and rediscovering purpose through AI. Jason opens up about going against expectations, getting laid off (again), and why community has become the most vital part of his entrepreneurial path.

This is a personal and practical conversation on how Jason helps business owners bring AI into their work in ways that are human, useful, and deeply thoughtful — including a clear "Three A's" framework you won't want to miss.

Don't miss this if you've ever wondered how to connect clarity, technology, and meaning — especially in times of uncertainty.

Show Highlights:

• Why Jason asks "What do you like to do?" instead of "What do you do?" [02:25]

• Growing up under pressure — and choosing his own way anyway [06:00]

• The defining moment: delaying graduation for a surprise study abroad [13:07]

• How getting laid off (again) led Jason to AI and entrepreneurship [17:24]

• The power of hiking, reflection, and reconnecting with community [20:13]

• Jason's clear and useful "3 A's" framework for AI: Automation, Answers, Advice [30:00]

• His #1 tip to beat prompt paralysis — "Have AI interview you" [34:14]

• Why connection is core to Jason's business philosophy [27:22]

For more updates and my weekly newsletter, hop over to https://betterquestions.co/

To learn more about Jason Yeh, check out the websites below:

https://scalingfreedom.ai/

https://www.linkedin.com/in/jasonjyeh/

Continuing from last week, today we discuss the fascinating ideas from Eric Nehrlich's book, challenging how we perceive problems and revealing the empowering potential of our choices.

This episode takes you through Eric's unique journey from the corporate world to a coaching career, where he blends varied methodologies for life-changing results. Learn how to confront personal fears and make decisions that truly matter.

Don't miss out on the chance to gain insights that can redefine your approach to both personal and professional challenges.

Show Highlights:

• This is the only thing you can control [03:16]

• What is the meaning of accepting your reality? [09:49]

• Would you want your child to stay at a job he hates? [12:36]

• Discover a holistic approach towards coaching [14:31]

• Learn about Eric's journey of coaching executives [19:52]

• Discover the real job of a coach [20:04]

• What are the unconscious fears that hold leaders back? [21:56]

• This is how you can get over your fears [25:32]

For more updates and my weekly newsletter, hop over to https://betterquestions.co/

To learn more about Eric Nehrlich, check out the websites below:

https://www.toomanytrees.com

https://www.linkedin.com/in/nehrlich

https://www.toomanytrees.com/book

In this episode, Dan sits down with the fascinating Eric Nehrlich. Eric's journey from an esteemed position at Google to becoming a sought-after executive coach is nothing short of inspiring.

Discover the rare blend of skills that make Eric a standout in both business strategy and personal development. Learn how a tragic accident prompted a career shift that now helps others reach their peak potential.

Tune in to hear Eric's intriguing story and gain insights that just might change the way you approach your career and life.

Show Highlights:

• Discover how Eric secured a job at Google [04:57]

• How are business, strategy, and leadership connected? [10:22]

• Discover the superpower of simplifying things for others [13:01]

• Learn Eric's journey of getting into executive coaching [14:43]

• Do you know incremental and non-incremental growth? [18:12]

• This is how you bring in innovation [20:11]

• Are you stuck in a cycle of limiting beliefs? [21:56]

• What drives bold career moves? [27:50]

For more updates and my weekly newsletter, hop over to https://betterquestions.co/

To learn more about Eric Nehrlich, check out the websites below:

https://www.toomanytrees.com

https://www.linkedin.com/in/nehrlich

https://www.toomanytrees.com/book

Continuing from last week, today's episode features the dynamic Richard Walsh, a seasoned marketing agency owner turned business coach. Imagine finding an extra $100,000 in profit sitting right there in your business—Richard knows where to look without extra marketing expenses.

He will offer practical strategies on juggling clients and feeling stuck as business owners. We'll explore compelling insights from his journey and how he's reshaping the way we think about success.

Curious to learn how to make your business work for you? This is an episode you won't want to miss.

Show Highlights:

• Do you feel stuck as a business owner? [01:43]
• This is the mindset you must have to achieve more [03:42]
• How does Richard find inherent money inside businesses? [07:44]
• Are you utilizing these business analysis tools? [08:43]
• Is a business all about sales? [11:22]
• The role and importance of accountability [15:06]
• Explore the world of Sharpen the Spear Coaching [17:50]
• This can be your key to increased profits and revenue [19:43]

For more updates and my weekly newsletter, hop over to https://betterquestions.co/

To learn more about Richard Walsh, check out the websites below:

https://sharpenthespearcoaching.com/

This week, we're featuring Richard Walsh, the mastermind behind Sharpen the Spear Coaching. With a wealth of experiences to draw from, Richard helps small business owners make significant changes without spending any extra money.

His unique approach combines a warrior's mentality with smart business strategies, making this conversation an insightful experience for entrepreneurs at any stage.

Tune in as we explore the art of balancing personal grit with professional acumen, guided by Richard's fascinating journey and seasoned advice.

Show Highlights:

• Discover what it takes to be a coach [02:18]
• Learn about the concept of sharpening the spear [03:51]
• What do martial arts teach about running a business? [05:48]
• Discover Richard's journey of resilience and reinvention [07:47]
• How are fitness and leadership connected? [12:11]
• Learn the importance of building routines and methods [14:18]
• This is how you can alleviate anxiety [15:20]
• The most common mistake business owners make [17:05]

For more updates and my weekly newsletter, hop over to https://betterquestions.co/

To learn more about Richard Walsh, check out the websites below:

https://sharpenthespearcoaching.com/