POWERS Podcast Episode #386 Summary
Trent & Tyler Leon – Co-Founders, Tilden Capital
Host: Chris Powers
Release Date: May 20, 2025
Episode Overview
In this engaging and candid episode, brothers Trent and Tyler Leon, co-founders of Tilden Capital, return to the POWERS podcast for a deep dive into their impressive trajectory from elite junior golfers to Division I athletes, professional golf, and ultimately, high-level entrepreneurship in the oil and gas sector. The conversation, expertly moderated by host Chris Powers, threads together the Leon brothers’ rare family story, the relentless demands of excellence both in sports and business, and the pragmatic optimism that guides their approach to risk, leadership, and adaptation in an ever-changing industry.
While the first hour draws memorable stories and leadership lessons from their golf journey, the latter half delves into nuanced perspectives on oil & gas investing, capital allocation, risk discipline, and building enduring relationships in business.
Key Discussion Points & Insights
1. Family, Sports, and the Early Pursuit of Excellence
[03:29–23:18]
- Sibling Competition and Support: The conversation begins with sibling dynamics, with both brothers acknowledging their sister Taylor as the best golfer in the family, given her LPGA career and tenacity. (03:29–04:03)
- Upbringing in Golf: Growing up in Texas, the brothers reflect on how their father's twin-like closeness and positive approach shaped their competitive yet supportive relationship. (04:14–07:15)
- Family Anecdotes: The infamous “wedding ring sawed off” story highlights a family culture of healthy competitiveness and swift reconciliation. (07:31–09:53)
- Joining Gleneagles: Their skill developed rapidly after plugging into a high-achieving youth golf culture at Gleneagles Country Club in Dallas, playing alongside future collegiate stars. (09:53–11:43)
- Turning Point Moments: Tyler recalls his Texas State Junior win as a pivotal confidence boost (13:18), while Trent highlights holding his own against 18-year-olds at MCI Heritage as a marker of his growth (13:46).
“I never wanted Tyler to play bad. I just wanted to play better.” — Trent Leon [06:15]
2. The IMG Academy Experience and College Choices
[15:50–31:54]
- Transition to IMG: Trent’s academic struggles prompted their move to IMG Academy, even if Tyler wasn’t initially enthusiastic. A gift from their dad, “Who Moved My Cheese?”, instilled a lesson in adaptability. (15:50–17:54)
- Fellow Alumni: The brothers reminisce about notable contemporaries such as Casey Wittenberg, Ty Tryon, Sean O’Hair, and Peter Uihlein. (18:42–19:27)
- Gaming Recruiting: Both describe the early and often aggressive recruitment tactics of D1 collegiate programs. Mike Holder, legendary Oklahoma State coach, is remembered for his up-close recruiting approach. (24:05–25:38)
- Deciding on OSU: Both ultimately chose Oklahoma State after evaluating other top programs, valuing the culture, golf legacy, and the chance to play alongside friends. Tyler’s recruiting trip with future stars sealed the deal. (25:42–29:10)
- Family Reflection: Their unique journey—three siblings as D1 golfers—was fueled by their father's selfless investment and persistent belief in their potential. (31:54–35:18)
“Like, as a little kid, I thought I could run through a wall if my dad told me I could. He just built it up.” — Trent Leon [34:00]
3. Collegiate and Professional Golf Realities
[35:33–47:31]
- Championship Wins: Both reminisce on the nerves and intensity of chasing and winning the 2006 NCAA Championship at Oklahoma State [37:03–37:48].
- Pro Career Lessons: The brothers reflect on the realities and relentless competition in professional golf. Tyler’s “aha moment” came in a PGA Monday qualifier, realizing that even world-class players often grind for minimal financial reward—prompting him to redirect his career. (42:23–44:41, 43:28 Notable Quote)
- Gracefully Moving On: Both brothers explicitly reject regret, proud of their commitment to golf and equally energized to transfer that discipline into their next venture. (44:03–47:31)
“If you’re the 400th best golfer, you’re worth like $70,000…and you’re really good. You shoot under par all the time...That was an aha moment.” — Tyler Leon [43:40]
4. Oil & Gas: Adaptation, Risk, and Value Creation
[48:38–75:29]
- Industry Landscape and Policy Impact: The Leons explain how U.S. political cycles impact oil and gas investment, especially regarding investor confidence and long-term capital. Despite lower prices, optimism is growing with a pro-energy administration. (48:38–50:53)
- Permian Basin & Inventory: They discuss evolving perceptions of tier-one inventory in the oil-rich Permian, noting both the resource’s resilience and the ever-expanding application of new tech to revive overlooked plays (e.g., the “new” Barnett shale in the Permian). (51:58–54:44)
- Risk Approach: Known for “paying too much”, Trent and Tyler clarify their risk/reward framework—seeking option value in properties others deemed too risky, and likening this to going for a par-5 in two. Their focus is absolute dollar return, not just IRR, and they often underwrite “bonus” zones for future upside. (55:18–58:00)
“Golf was a great example of risk/reward. Should I go for this par five with the 3-iron in my hand over water, or should I lay up?” — Tyler Leon [57:55]
- Navigating Regulation: They detail the complexities of federal land, environmental constraints (highlighting the “prairie chicken” issue), and the shift toward operator prudence and free cash flow. (58:32–62:26)
- Team & Leadership: Tilden Capital runs extraordinarily lean—with 13 core staff—by leveraging trusted partners (notably Pegasus) and personally pricing most deals. They view keeping a small, capable team as a strategic advantage. (64:09–68:18)
“Big deals take the same amount of time as little deals, so work on big deals. And relationships matter…That’s what our dad always told us.” — Tyler Leon [71:02]
- Relationship-Driven Business: Tilden’s edge in acquiring large family mineral deals traces to years of relationship-building, trustworthiness, and a long-game mindset, as opposed to transactional opportunism. (68:18–72:00)
- Simplicity & Focus: Despite distractions, the Leons remain laser-focused on their core mineral acquisition business, resisting the “shiny object” trap of expanding into unrelated investments. (72:00–73:47)
- Future Outlook: They aim to stay land-driven but may eventually build a small operating team for select drilling ventures, while always maintaining their mineral-buying focus. (74:04–75:17)
Notable Quotes & Moments
- On family culture:
"He made...as a little kid, I thought I could run through a wall if my dad told me I could. He just built it up..." — Trent Leon [34:00]
- On risk in golf vs. business:
“Golf was a great example of risk/reward. Should I go for this par five with the 3-iron in my hand over water...?” — Tyler Leon [57:55]
- On being world-class but not wealthy:
“If you’re the 400th best golfer, you’re worth like $70,000...and you’re really good.” — Tyler Leon [43:40]
- On relationships and big deals:
“Big deals take the same amount of time as little deals, so work on big deals. And relationships matter.” — Tyler Leon [71:02]
Important Timestamps
- Sibling & Family Golf Stories: [03:29–14:18]
- IMG Academy & College Choices: [15:50–31:54]
- Oklahoma State & Winning Mentality: [35:33–39:03]
- Pro Golf Financial Realities / Transition: [42:23–47:31]
- Oil & Gas Industry Landscape/Policy: [48:38–51:53]
- Permian/Tier 1 Inventory & Barnett: [51:58–54:44]
- Risk/Reward Framework: [55:18–58:00]
- Team Structure & Leadership: [64:09–68:18]
- Long-Game Relationship Building: [68:18–72:00]
- Focus and Future Strategy: [72:00–75:17]
Tone and Takeaways
The Leon brothers’ banter and humility, combined with Chris Powers’ informed curiosity, make the podcast accessible and inspiring. The episode is full of actionable insights on discipline, risk-taking, team design, and the power of sustained relationship-building, all delivered with the straight-talk, understated confidence, and thoroughly Texan optimism characteristic of POWERS guests.
For builders, investors, athletes, and operators alike, this conversation radiates both practical wisdom and an indomitable attitude toward “grinding it out” at the highest level—whether on the golf course or in the boardroom.
Recommended For:
Entrepreneurs, investors, young athletes, oil & gas professionals, or anyone interested in personal growth, risk management, and the compounding value of discipline and relationships.