In this episode, I share what I've learned from simultaneously running a 7-figure coaching business and launching Tiger Rock Capital Management, my hedge fund.

I walk through my journey from working as the first outside hire at a hedge fund in 2013, to building my coaching practice in 2016, to scaling it to consistent six-figure months, and finally launching my own fund after putting up strong returns in 2023-2024.

Key lessons covered:

• Why one business is more than plenty (and when two might work)
• How the core skills of entrepreneurship transfer across completely different industries
• The critical importance of saying NO to the wrong clients
• Why you need a world-class operational partner before starting a second business
• How grit and resilience matter more than industry expertise

Whether you're thinking about starting your first business, scaling your current one, or considering a second venture, this episode breaks down the realities of what it actually takes.

P.S. Whenever you're ready, here are 2 ways I can help you:

1. Business Coaching for Coaches & Online Entrepreneurs

If you're a coach or online business owner looking to scale to consistent $25K-50K months, I can help. I've helped clients go from sporadic $5K months to reliable $40K+ through proven systems for lead generation, sales, and client delivery.

Book a call: BrendanHBurns.com/call

2. Institutional-Quality Hedge Fund Management

If you're a high-net-worth individual looking for hands-off, professional investment management, Tiger Rock Capital Management delivered 24% net returns in 2024. This isn't for DIY stock pickers, this is for people who want capital allocation handled by someone who lives and breathes markets.

Learn more: TigerRockCapitalManagement.com/call

From a small town in Eastern Kentucky to advising on over $1.5 trillion in M&A transactions, Jim Woolery's career journey is worth tracking. As a former Senior Partner at elite law firm Cravath, Swaine & Moore LLP, Co-head of M&A at JP Morgan, and hedge fund founder, Jim shares the strategic decisions and bold moves that shaped his extraordinary career.

In this episode, Jim reveals:

• The one simple thing you must do to make partner at a top law firm
• How he transitioned from law to investment banking at the highest levels
• Why he left a prestigious partnership to keep challenging himself
• The "country lawyering" tactics that closed billion-dollar deals
• His framework for prioritizing the 3 critical elements in every transaction
• Why he founded his own advisory firm after hedge fund success

Jim's story demonstrates the power of continuous learning, strategic risk-taking, and staying ahead of market trends. Whether you're climbing the corporate ladder, considering a career pivot, or building your own firm, this conversation offers invaluable insights from someone who mastered multiple industries at their pinnacle.

Connect with Jim: 917-841-4832 | https://www.wooleryco.com/

Topics: Career transitions, M&A, corporate law, investment banking, hedge funds, entrepreneurship, leadership

In this episode, I join Erik Berglund (a former client and host of I Have Some Questions…) for a deep dive into what truly drives fulfillment. We unpack my path from Wall Street to building a seven-figure coaching business and now scaling his hedge fund, Tiger Rock Capital Management.

Topics include:

• The hidden gap between external success and internal satisfaction

• What makes a coaching business actually scalable

• Why emotional regulation and identity drive real results

• How to know when it’s time to go all-in on yourself

I also share how my background — including a JD-MBA, years in finance, and hundreds of thousands invested in coaching and therapy - shaped my mission and mindset.

🎧 Plus, stay tuned for upcoming episodes featuring Dre Baldwin (former pro basketball player) and Jim Woolery (former Cravath partner and co-head of JPMorgan’s M&A group).