"I Didn't Have Any Idea What I Was Spending": Nearly Burning Through a $13M Exit

Ryan Begelman made $13 million from his Bisnow exit but found himself spending $800,000 annually with no tracking system, learning hard lessons about wealth management.

Key Takeaways

• Financial expertise doesn't automatically translate to personal wealth management and investment discipline
• Spending $67,000 monthly without tracking led to dangerous lifestyle inflation despite substantial net worth
• Keeping 80% of wealth in cash instead of investing cost millions in potential returns over time
• Life coaching became both a lucrative career pivot and personal development investment worth six figures annually
• Professional financial modeling revealed spending patterns that threatened long-term security despite initial comfort
• Cutting monthly expenses from $67,000 to $30,000 required eliminating luxury vacations, summer homes, and premium services
• Entrepreneurial burnout often stems from poor communication and boundary-setting rather than just overwork
• Family money patterns strongly influence spending behaviors even among financially sophisticated individuals
• Respecting money as stored energy prevents wasteful spending that disregards previous work and sacrifice

Timeline Overview

• 02:32–06:09 — Ryan's Early Career and Bisnow Success: Background at Carlyle Group private equity, risking $250,000 savings to buy into Bisnow, growing it from $1.5M to $20M revenue before $51M exit generating $13M personally
• 06:09–09:37 — Financial Mismanagement and Realizations: Despite finance background, kept 80%+ wealth in cash earning 1-2% instead of investing, missing massive market gains while waiting for next business opportunity that never materialized
• 09:37–12:38 — Family Influence and Flashy Spending: Father's boom-bust business cycle and cash-heavy lifestyle influenced Ryan's spending patterns, leading to $3,000/night hotels and private chefs without expense tracking
• 12:38–20:05 — Life Coaching and Personal Epiphany: Discovered coaching after seeking $1M annual income with 20-hour work weeks, invested six figures learning the craft while addressing personal development needs
• 20:05–20:45 — The Start of a Coaching Journey: Built coaching practice from 12-19 clients at $4,000/month each, creating sustainable income model that provided first real sense of financial security
• 20:45–22:44 — Financial Success and Security: Combination of invested assets and $600,000 coaching income finally created mathematical confidence about long-term financial viability
• 22:44–23:17 — Existential Financial Concerns: Despite surface-level financial success, underlying anxiety about running out of money prompted deeper analysis of spending and investment strategies
• 23:17–26:56 — Modeling for Financial Future: Professional Monte Carlo analysis revealed spending levels unsustainable long-term, forcing recognition that simple Excel models were inadequate for complex financial planning
• 26:56–32:38 — Spending Adjustments and Reflections: Cut monthly spending from $67,000 to $30,000 by eliminating luxury travel, summer home, premium services while learning to respect money as stored energy
• 32:38–38:24 — Endurance and Self-Care in Business: Lessons about sustainable entrepreneurship, avoiding burnout through better communication and boundary-setting rather than stoic perfectionism

From Private Equity to Entrepreneurial Success

• Ryan built his foundation working at Carlyle Group, one of the world's largest private equity firms, spending a decade learning business fundamentals and real estate investment strategies before taking the entrepreneurial leap.
• He discovered Bisnow through cold outreach to founder Mark Bisnow, negotiating a deal to buy into the commercial real estate media company and grow it together rather than starting from scratch.
• "I cold reached out to them to see if they would sell me the business and ultimately cut a deal where we would sort of grow it together and sort of bought into the business a bit grew the business bootstrapped it from when I joined it was at 1.5 million in revenue and grew it to over 20 million."
• The risk paid off dramatically when Ryan invested his entire $250,000 savings into Bisnow and Summit, living on just $6,000 monthly while reinvesting everything back into business growth and operations.
• Over seven and a half years, Bisnow generated $64 million in total distributions including $13 million in cash flow during Ryan's ownership and $51 million from the final sale to private equity.
• His success with Summit and Powder Mountain ski resort provided additional liquidity through strategic exits, though he describes those returns as "small sums" relative to the Bisnow windfall.

Financial Expertise Doesn't Guarantee Personal Discipline

• Despite his extensive background in private equity and financial modeling, Ryan made fundamental mistakes with his personal wealth management that cost him millions in potential returns over multiple years.
• "I think I suffered from thinking I knew everything," Ryan admitted, explaining how entrepreneurial confidence led him to believe his business success would automatically translate to investment expertise.
• He kept over 80% of his $13 million in cash and his primary residence, earning just 1-2% returns in high-yield savings accounts while the S&P 500 averaged 13% annual returns during the same period.
• The decision to avoid market investment stemmed from his plan to acquire another company, but when that opportunity never materialized, he woke up realizing he "would be worth twice as much now if I had just been in the market."
• Ryan's approach to personal finance was surprisingly unsophisticated despite his professional expertise: "All I had was a stupid little spreadsheet where every like on random dates I would go through all my various bank accounts and things and I would add up my net worth."
• This disconnect between professional competence and personal financial management represents a common trap for successful entrepreneurs who assume their business skills automatically transfer to investment strategy.

Family Patterns and Untracked Lifestyle Inflation

• Ryan's spending behaviors closely mirrored his father's patterns, who built wealth through cash-heavy businesses but experienced dramatic boom-bust cycles that shaped the family's relationship with money and security.
• "My dad thought he was rich because like he could play tennis he belonged to like a country club and but in truth when she met him because he had income he just had income," Ryan explained about his father's cash-flow-rich but asset-poor approach.
• His father's business empire collapsed during the late 1980s recession due to overleveraging, creating years of financial stress that deeply influenced Ryan's later anxiety about running out of money despite substantial wealth.
• Ryan's own spending escalated without awareness or tracking: "I didn't have any idea what I was spending only only thing I tracked was my net worth," leading to peak monthly expenses of $67,000 or $800,000 annually.
• Luxury spending included $3,000 per night hotels, private chefs, mariachi bands for home entertainment, and a $155,000 Burning Man experience, all justified as occasional treats that became habitual lifestyle inflation.
• The lack of expense tracking meant Ryan missed how seemingly small decisions compounded: property insurance ($25,000 annually), handyman services ($50/hour for monthly visits), and premium travel choices that accumulated without conscious evaluation.

Life Coaching as Career Pivot and Personal Development

• Ryan's transition to life coaching emerged from his search for a business model generating $1 million annually while working fewer than 20 hours per week, leading him to discover the economics of high-end coaching.
• A coach he interviewed charged $4,000 monthly for 280-minute sessions (80 minutes twice monthly), creating a $600,000+ annual income model that seemed both lucrative and aligned with Ryan's mentoring interests.
• "It became this really beautiful virtuous cycle where the more I coach like it sort of forces me to become a better more virtuous version of myself," Ryan explained about the personal growth benefits beyond financial rewards.
• Ryan invested heavily in his coaching education, spending nearly $200,000 some years on training, classes, and working with other coaches and therapists to develop his skills and personal awareness.
• His coaching practice grew rapidly from 12 to 19 clients at peak, generating approximately $600,000 annually while providing the first genuine sense of financial security he had experienced despite his previous business success.
• The combination of coaching income and properly invested assets created mathematical confidence about long-term financial viability that his previous cash-heavy approach had never provided, even with larger absolute wealth.

The Wake-Up Call from Professional Financial Modeling

• Ryan's financial reality check came when he moved beyond simple Excel spreadsheets to professional Monte Carlo modeling that revealed unsustainable spending patterns threatening his long-term security.
• "I started interviewing financial advisers to see if like they could help me double check that I was on the right path and in the process I learned more about how they use software models to analyze all this."
• The professional analysis was "more pessimistic and presumably more accurate" than his homemade projections, incorporating tax implications, market volatility scenarios, and retirement withdrawal strategies his simple models had ignored.
• This modeling revealed that despite his substantial net worth, his current spending trajectory combined with conservative investment approach created significant risk of running out of money before death.
• The analysis forced Ryan to confront family patterns of financial insecurity: "I watched my grandparents on both sides run out of money before they died and have to be supported by their children."
• Professional financial planning software provided the objective analysis needed to overcome the psychological biases and wishful thinking that had characterized his previous financial decision-making approach.

Dramatic Spending Reduction and Money Respect

• Ryan cut his monthly spending from $67,000 to approximately $30,000 by systematically eliminating luxury expenses that provided minimal happiness while consuming substantial resources over time.
• Major cuts included expensive vacations, his summer home, premium pet care services, business class flights, excessive Burning Man spending, clothing purchases, handyman services, home organization, and impulse Amazon purchases.
• "The way I think about it now is I didn't really respect money," Ryan reflected, describing his new approach of treating money as stored energy that deserves the same respect as physical energy.
• He implemented a one-week waiting period for Amazon purchases, allowing impulse buying desires to fade and revealing how many seemingly necessary items were actually unnecessary wants driven by YouTube marketing.
• His current $360,000 annual spending breaks down to $120,000 for housing (property taxes, insurance, repairs), $105,000 for coaching education and business expenses, and $140,000 for personal expenses.
• Ryan considers selling his Williamsburg townhouse despite loving its amenities (sauna, cold plunge, steam room) to achieve even greater financial freedom and redirect resources toward discounted coaching for clients who cannot afford full rates.

Sustainable Entrepreneurship and Burnout Prevention

• Ryan's entrepreneurial burnout stemmed primarily from poor communication and boundary-setting rather than excessive work hours, leading to relationship strain with business partners and personal anxiety.
• "I wish I had learned a little earlier to just have a little bit more self-kindness to have more self-knowledge to know some of what sort of I'm sensitive to some things that maybe don't bother other people but bother me."
• His perfectionist approach included trying to be "the stoic manly even keled nothing bothers me" leader while internally struggling with anxiety about financial security and business decisions affecting the company.
• Poor communication patterns involved holding concerns internally until reaching a breaking point, then delivering critical feedback in unproductive emotional states rather than addressing issues constructively when they first arose.
• Ryan's financial anxiety often made him overwhelming to business partners: "I'd be calling them and being like guys we're gonna miss payroll we got to do and I would be freaking them I'd be like kind of like overwhelming."
• His coaching work taught him "both/and" thinking rather than binary approaches, allowing for collaborative problem-solving that honors different perspectives rather than forcing singular solutions through conflict.

Conclusion

Ryan Begelman's journey from $13 million exit to near financial crisis illustrates how wealth without systems creates dangerous illusions of security. Despite his private equity expertise, Ryan fell into classic post-exit traps: lifestyle inflation, cash hoarding, and spending without tracking. His transformation required professional financial modeling to reveal the truth about his trajectory, plus personal development work to address the underlying patterns driving his financial behaviors.

The combination of systematic expense reduction and sustainable income through coaching created the genuine security that raw net worth alone had failed to provide.

Practical Implications

• Track all expenses meticulously regardless of net worth, using detailed categorization rather than relying on credit card statements or rough estimates
• Invest liquid assets immediately after exits rather than waiting for perfect timing or future business opportunities that may never materialize
• Implement professional financial modeling with Monte Carlo analysis to understand true long-term sustainability beyond simple spreadsheet projections
• Establish spending guardrails based on scientific withdrawal rates (3-4%) rather than assuming high net worth eliminates need for budgeting discipline
• Address family money patterns through therapy or coaching before they unconsciously drive expensive lifestyle decisions that undermine financial security
• Build sustainable income streams that align with personal interests rather than relying solely on asset appreciation for long-term financial health
• Practice direct communication about financial concerns with business partners rather than letting anxiety build to explosive confrontations
• Respect money as stored energy from previous work, making spending decisions that honor the effort required to earn those resources
• Plan for post-exit identity and purpose through coaching or other development work rather than assuming financial success automatically provides fulfillment