Coffeez for Closers with Joe Shalaby

Episode: “100M+ Exit ft. Alexis Sikorsky” (August 22, 2025)

Host: Joseph Shalaby
Guest: Alexis Sikorsky (serial entrepreneur, exited for $100M+)

Episode Overview

In this episode, host Joseph Shalaby welcomes Alexis Sikorsky, a seasoned entrepreneur who has built, scaled, and exited businesses, including a $100M+ exit. They dive deep into the emotional and practical realities of entrepreneurship: navigating high-stakes crises, managing people, learning from major business mistakes, demystifying private equity, and building frameworks to help founders achieve their own successful exits. Alexis is candid about his failures, personal struggles, and the realities (not the glamour) of entrepreneurial life, blending unfiltered wisdom with practical advice.

Key Discussion Points & Insights

1. Embracing the Entrepreneurial Path Early

• Early Ventures: Alexis began entrepreneurial ventures at 15, starting with import/export. He jokes his motivation was adolescent overconfidence:
  • “I thought I was very, very smart. That’s something all 15 year olds have in common.” (01:17 – Alexis)
• Both host and guest shared stories of their failed teenage startups, emphasizing the importance – and inevitability – of early failure.

2. Running & Scaling Tech Companies Before and After Crisis

• Growth Pre-Crisis: Alexis built and grew a banking software company from the basement, reaching $12M revenue by 2008 (“I’m the king of the world. I’m so smart, I’m so bright.” 05:11 – Alexis).
• Impact of the 2008 Crash:
  • Lost 75% of revenue overnight, as banks froze all tech spend (05:42).
  • Emotional toll revealed: “I had to grind from 2008 to 2014; I mortgaged my house every month. You ask: are we throwing good money after bad?” (06:22 – Alexis).
  • Survival strategies: Firing 75% of staff, slashing expenses, pivoting to new, “countercyclical” products focused on compliance and risk (07:39).

3. Hardest Parts of Leadership – Letting People Go

• Pain of Layoffs: Alexis confesses that firing people made him “physically sick...literally” and that the effects on founders can be overwhelming (02:40).
• Approach: Deals with it “as humanly as possible” and distinguishes between firing for performance (“their fault”) and economic reasons (“your fault”) (03:06).

4. Hard Lessons in Business

• Says he “left $50 million on the table” due to not understanding private equity (PE) and various mistakes (09:01).
• Now, Alexis helps founders avoid these mistakes, especially by teaching them to “speak private equity.”
• On PE:

  “It’s a leverage business… exactly like buying a house, except your leverage is a little lower. You get like 70% leverage, not 90. And it’s a little higher risk, but it’s way, way better rewards.” (12:50 – Alexis)

5. The Apex Method for Cashing Out

• Genesis: After selling his business and three-year retirement, Alexis noticed founders making the same mistakes he had. He started helping, then wrote a book so more people could benefit (13:47 – 14:45).
• Core Steps:
  1. Analyze: Deep-dive into the company; most founders “don’t know what they have.” (15:15)
  2. Plan: Set precise strategic goals, e.g., valuing growth targets for a 4-year exit timeline.
  3. Execute: Founder executes; Alexis joins the board, tracks progress.
  4. Exit: Target is a transformative exit in under 4 years.
  • “Lots of them have massive engines and no steering wheel.” (15:51 – Alexis)

6. Emotional and Ethical Challenges

• Personal Impact of Hard Decisions: Recalls firing half the company (twice) due to Swiss regulations—“that’s hard” (19:29 – 20:24).
• Family & Grit: Admits he’s at a loss teaching resilience to kids raised in affluence ("I don’t know how to explain to a kid that’s been brought [to] school in a Bentley that you need to grind" 28:47).

7. Internal Hurdles for Founders

• No Strategic Plan: Most don’t know what they want personally (20:50).
• Confusing Urgency and Importance: “You spend your time extinguishing fires instead of doing strategy” (21:05).
• Undercapitalized: Alexis insists on “nine months of your monthly burn rate in your bank account,” as crisis is inevitable.
• People Constraints: Hard to attract talent needed to scale, especially for mid-size businesses. Solution: “Virtual C-suite” with fractional, often semi-retired, experienced execs (23:08).

8. Leadership vs. Management

• Alexis learned post-exit that he’s not a manager, but a leader: “People confuse manager and leader…they’re kind of opposite skills. Very rarely do you meet someone who’s both” (24:40).

9. The Meaning of Freedom and Life After Exit

• Freedom: “Freedom is a number… how much money do you need in your bank account to never have to work again?” (26:05).
• He always asks founders: “What’s your number?”—that’s the minimum target for the sale.
• On ‘Now What?’ Post-Exit: Wryly dismisses self-pity: “Boo hoo… now you have $40 million…get over it… Go see a shrink you can afford” (27:04).

10. What Alexis is Most Proud Of and Advice for Young Entrepreneurs

• Pride: More proud of helping others and his book than his own financial exit.
  • “Pride comes from helping others, not from your own success.” (27:38)
• Advice: “Know what you don’t know. Know what you’re good at, know what you’re bad at and have a plan.” (28:12)

11. Parenting and Values

• Teaching Children: Acknowledges struggle raising grit in affluent kids. Focuses on values of responsibility and charity rather than displays of wealth.
  • “You can be rich, you’re not allowed to be an asshole.” (30:24 – Alexis)
  • “With money comes responsibility.”

12. Personal, Family, and Professional Goals

• Personal: Addressing his ADHD, which strains family and friends (31:25).
• Family: Supporting his daughter with ASD, helping her flourish (32:06).
• Professional: Help founders to successful exits. “I don’t have a set number or money goal.” (32:27)

Notable Quotes & Memorable Moments

• On firing people:
  “Makes me physically sick every time I have to do it.” (02:40 – Alexis Sikorsky)
• On what keeps founders in a rut:
  “Needing good people. Not being able to afford good people. That’s the one that… keeps most companies in the $10 million range.” (22:37 – Alexis)
• On leadership:
  “They confuse manager and leader…they’re not the same, but kind of opposite skills.” (24:40 – Alexis)
• On what he tells his kids:
  “You can be rich, you’re not allowed to be an asshole.” (30:24 – Alexis)

Timestamps for Important Segments

• 00:29 – Alexis’s morning routine (or lack thereof with young kids)
• 01:04 – Alexis’s first venture at 15
• 02:11 – Most difficult early fears: firing people
• 05:03 – 06:53 – Growth, crash, and bounce-back of his tech company post-2008
• 09:01 – Realizing he lost $50M due to mistakes with PE
• 10:38 – 12:32 – Private Equity crash course
• 13:32 – 15:15 – The APEX method: birth and core concepts
• 19:29 – Firing half the staff due to Swiss law—emotional trauma
• 20:50 – 23:08 – Biggest founder hurdles: lack of plan, urgent vs. important, undercapitalization, talent
• 24:40 – Discovering the difference between leaders and managers
• 26:05 – “Freedom is a number”
• 27:38 – What Alexis is most proud of: his impact helping others
• 28:47 – 31:14 – Teaching children values; instilling grit and social responsibility

Tone and Final Thoughts

The conversation balances humor, humility, and hard truths. Alexis is candid and dryly witty, unafraid to highlight his own missteps as much as his wins. Listeners come away with practical frameworks for scaling and exiting a business, wisdom on emotional resilience, and a reminder that success isn’t just about money—it’s about the legacy you build by helping others.

Find Alexis Sikorsky: On LinkedIn (search his name)
His Book: “The APEX Method for Cashing Out” – Available on Amazon/Audible

For any entrepreneur, founder, or leader, this episode is a powerhouse of truth, humility, and actionable advice from someone who’s truly “been there, done that.”