Founder Finances: Wealth, Life, & the Meaning of “Enough” w/ Chris Girbés of Five Oceans Advisors

Summary

In this episode, Chris Girbés, founder of Five Oceans Advisors, unpacks his unconventional journey into entrepreneurship and his distinctive approach to financial advising for founders. Chris shares how he transitioned from a traditional, salary-based career in wealth management to starting his own advisory firm from scratch with zero clients and no prior sales experience. His entry into entrepreneurship wasn’t the result of a lifelong dream, but rather a combination of necessity and conviction that he no longer fit the corporate mold. Chris dives into the early years—maxing out credit cards, grinding through coffee meetings, and building a business from nothing during one of the most transformative times of his life.

As the episode progresses, Chris outlines how he eventually found his niche by serving young, high-growth founders. He explains how differentiating his wealth management practice wasn’t about flashy marketing or lofty slogans, but about deeply understanding the mindset and needs of the clients he serves. Chris emphasizes the importance of liquidity planning, resource management, and helping clients articulate what “enough” looks like in their financial lives. He also offers a candid look into his firm’s philosophy, including the value of financial life planning and their internal alignment on offering both technical expertise and emotional intelligence in client relationships.

Chris wraps up the conversation by offering practical insights for other founders—discussing hiring, scaling, and how the story doesn’t end at a business exit. From the risk of post-exit depression to the need for a strong “protective reserve,” Chris reframes traditional financial advice for the entrepreneurial context. Whether you’re building your first business or preparing for an exit, this episode is rich with firsthand experience, hard-won insights, and a deep understanding of the challenges, and opportunities, entrepreneurs face.

Takeaways

1. Starting a business doesn’t require a perfect plan—sometimes necessity and momentum are enough to get going.
2. The biggest mismatch in expectations was how long everything would take—success is always slower than you think.
3. Early growth often comes from saying “yes” to everything and offering genuine value without asking for anything in return.
4. Your first hire doesn’t need to be perfect—look for a “Swiss Army Knife” who is hungry to learn and grow.
5. Founders often mistake control for lower risk—being concentrated in your business may feel safer but carries hidden dangers.
6. Lifestyle creep can silently erode the ability to reinvest in your company—spend intentionally.
7. The strategy to get rich (take risk) is different from the strategy to stay rich (diversify).
8. Define your “walkaway number”—know what’s truly enough for you, or risk chasing an unachievable moving target.
9. Selling your company is not the end of the story—many founders face a deep emotional crash post-exit without a clear next chapter.
10. Differentiate by specializing—generalist advisors offer less value than those who deeply understand your world.

Chapters

• [00:01] Chris’s Unconventional Entry Into Entrepreneurship
  • Chris shares how he stumbled into business ownership by necessity rather than design, starting with a carpet cleaning business while training for football.
• [03:05] From Salary to Startup: The Shift That Sparked Five Oceans
  • His decision to walk away from a stable job and launch his own wealth management practice was rooted in a desire for autonomy and a bet on himself.
• [05:23] Why He Didn’t Seek a Co-Founder and Just Got Started
  • Chris explains why he didn’t look for a co-founder at the beginning—he simply needed to move fast and start generating income.
• [06:39] Reality Check: What Didn’t Match Expectations
  • He reflects on how building a business took much longer than anticipated and why runway and patience are essential for founders.
• [08:33] The “10,000 Cups of Coffee” Strategy for Growth
  • Chris leaned into relationship building and gave away his time to add value and eventually earn trust and clients.
• [11:54] Hiring the First Team Member and the Power of Delegation
  • The joy and leverage of hiring someone who could do things better than him became a catalyst for business momentum.
• [16:37] Differentiating in a Crowded Wealth Management Industry
  • Chris talks about his fee-only model, rejecting commission-based incentives, and building trust through a client-first approach.
• [20:33] Niche Focus on Young Founders and Specialized Services
  • He explains how working with early-stage founders led to specialized offerings like business continuity and exit planning.
• [25:04] Financial Life Planning and Resource Management
  • Chris describes Five Oceans’ broader view of wealth—managing time, energy, and money—and how they employ a full-time life strategist.
• [27:27] What Makes Founders Financially Unique
  • Chris outlines how founders differ from employees in terms of liquidity, risk tolerance, and reinvestment strategies.
• [32:52] Constant Advice: Stay in the Game Longer
  • Founders need more protective reserves than traditional employees to weather business volatility and maintain ownership.
• [36:19] Misconception: Life Ends at the Exit
  • Many founders assume everything gets easier after selling, but Chris warns of identity loss and post-exit emotional challenges.
• [47:10] Operating Philosophy: Always Tell the Truth
  • As an operator, Chris believes honesty—especially early and often—is foundational to building trust.
• [48:47] Scaling and the Caution of Lifestyle Creep
  • He cautions against unintentionally increasing lifestyle spending at the cost of strategic business reinvestment.
• [51:06] The Questions Founders Should Be Asking Their Advisors
  • Chris suggests founders ask how their advisor is truly differentiated and whether they specialize in working with entrepreneurs.
• [54:04] The First Week of a Career: Talk to Customers Immediately
  • Although initially unsure, Chris agrees that building conversations with real clients would have fast-tracked his learning.
• [56:22] Mentorship as a Superpower
  • He attributes much of his growth to proactively seeking mentors—especially those he wants to emulate—not just admire.