Podcast Summary: The Investor with Joel Palathinkal

Episode: Troy Rosales: Connexa Capital
Date: October 3, 2025
Host: Dr. Joel Palathinkal
Guest: Troy Rosales, Connexa Capital

Overview

This episode dives into the unique career journey and investment philosophy of Troy Rosales from Connexa Capital. Dr. Joel Palathinkal and Troy explore Troy's unconventional path from a blue-collar family and community college to Ivy League education, and from various investment banking and private equity roles to his current focus in venture capital. The discussion provides honest advice for aspiring investors, demystifies recruiting and diligence processes across finance roles, and contrasts data-driven New York venture approaches to more "vibe-driven" West Coast mentalities.

1. Troy’s Origin Story: From Blue-Collar Roots to Ivy League and Finance

Timestamp: [02:47] – [16:31]

• Family Background and Initial Aspirations:

  • Troy grew up in a blue-collar household; his father was a late-in-life UC Berkeley graduate who, upon entering high finance, became a key influence.
  • In high school, Troy set his sights on investment banking after learning about its income and prestige.

  "My dad was whispering, we were saying, hey, there's these guys called investment bankers that, you know, make a lot of money, they work a lot of hours, but could be something that you might be interested in." — Troy Rosales [03:29]

• Community College Hack and Ivy League Transfer:

  • Rejected by all top colleges out of high school, Troy attended community college, excelled academically and in extracurriculars, then transferred to Cornell University—a strategy he openly discusses.
  • Worked part-time jobs at CVS, laundromats, and as a lifeguard instructor while at community college.

• Cornell and Beyond:

  • Culture shock at Cornell, entering as a transfer student focused on getting a job rather than the classic college experience.
  • Landed an internship at Barclays, but COVID-19 disrupted immediate hiring opportunities.

2. Early Career: Investment Banking and Private Equity

Timestamp: [07:38] – [16:31]

• Presidio Technology Partners:

  • Landed first full-time banking role in a small team during the COVID-era ZIRP boom.

• Houlihan Lokey:

  • Benefited from a lateral hiring wave; exposed to a variety of sectors and deal work.
  • Emphasizes the value of hands-on execution and learning at scale.

• Platinum Equity:

  • Transitioned to large cap private equity, working on complex industrial and business services acquisitions.
  • Describes intense deal work (“went to LOIs on eight different deals, closed three”) and the toll it took.

• Personal Reset:

  • Realized the “juice wasn’t worth the squeeze,” left LA, traveled, reconnected with family, and reprioritized health and life.

  “Can I really be doing this for four or five years and lose all my hair and lose friends and relationships? I decided to just cut bait because I figured the juice was not worth the squeeze there.” — Troy [12:57]

3. The Transition: Connexa Capital and the Venture Mindset

Timestamp: [14:09] – [16:31]

• Joining Connexa via LinkedIn:

  • Advocates for LinkedIn Easy Apply (“don’t listen to the haters”) [14:09].
  • Attracted to Connexa after seeing real private equity rigor in their venture process—unlike less-disciplined, “fluffy” early-stage venture approaches.

• Fit and Investment Lens:

  • Prefers hands-on diligence and unit economics over thematic or hype-based investing.
  • Finds more long-term alignment in Connexa’s approach than in banking or traditional PE.

4. Life and Career Lessons: Skills, Values, and Personal Growth

Timestamp: [17:32] – [22:07]

• Formative Jobs and Transferable Skills:

  • Early work (CVS, lifeguard, laundromat, odd jobs) instilled reliability, discipline, and a willingness to take risks—with a story about learning Excel from an elderly artist’s husband.
  • Importance of humility and showing up (“if you’re working at CVS, don’t be on your phone. If you’re a lifeguard, be present.”) [20:23]

• Persistence and Motivation:

  • Emphasizes that goal orientation and drive are durable traits, but must be nurtured like a muscle.

  "If you are a motivated individual, like that stuff feels like depression to you sometimes where you’re not on the same grind set that you were before." — Troy [20:23]

• Community College Transfer Strategy:

  • Notes that Ivy League transfer admits are rare and schools often seek unconventional, high-achieving backgrounds.
  • Prepares listeners for DIY aspects of the “hack” and highlights the soft advantages (smaller pool, untraditional path).

5. Culture Shock & Networking in Elite Schools

Timestamp: [25:16] – [29:45]

• Competitive, Career-Oriented Atmosphere:

  • “Everything was oriented to getting a job from the school… gossip between a lot of the job nerds is like, hey, where’s Troy working full time?” [26:32]

• Contrast with Community College:

  • Community college emphasized academics and survival over networking.
  • At Cornell, it’s about landing internships and joining clubs (though as a transfer, Troy faced “classism” and exclusion from established clubs).

6. Insider’s Guide to Recruiting: Banking, Private Equity, and Venture

Timestamp: [29:45] – [45:09]

Investment Banking:

• Lateral and full-time interviews mostly focus on actual deal experience, not just technicals or canned questions.

• LBO or DCF case studies for laterals; speed and “chemistry” are key.

  “If they are opening up for hire for laterals, that means the group is sweaty and they need bodies quickly and whoever can do the process in two weeks and you’re not weird, the job is frankly yours.” — Troy [31:23]

Private Equity:

• Process is more cookie-cutter: deal walk-throughs, paper LBOs, live case studies, and a model-building assignment.
• Emphasizes chemistry and cultural fit as a differentiator given how much time is spent together (“airport test”).
• Firms may use informal coffee chats to gauge personal fit: “Knives are down, guns are down… we’re just chatting like buddies.” — Troy [37:05]

Venture:

• Venture processes are more variable and network-driven; at Connexa, diligence, unit economics, and deal substance over “vibe.”

7. Financial Modeling: Building Skills and Best Practices

Timestamp: [42:46] – [45:09]

• Recommends starting with templates, debugging existing models, building from scratch, and maximizing “reps.”

• YouTube and online courses are now powerful, democratizing resources.

  “Building from scratch is the best way to understand any financial model… I found YouTube to be very powerful.” — Troy [43:50]

8. Market Trends and Investment Philosophy

Timestamp: [45:21] – [58:07]

• Private Equity “Game of Hot Potato”:

  • Large sponsors often buy from each other; true value is created earlier (lower middle market, strategic add-on M&A).

• Connexa’s Approach:

  • Focus on strong economic fundamentals in venture (“a lot more common in New York than SF”).
  • Minimum $1M ARR, focus on logo retention, net dollar retention, LTV/CAC, and businesses at a real growth inflection.
  • Reluctant to play the “power law” (few bets, huge returns) approach of some Silicon Valley VCs; seeks consistent returns, minimizes zeros, and underwrites for 2–4x exits.
  • Leans on co-investment and deep diligence thanks to robust LP/fund network.

  “Every single deal that we underwrite too is like at a healthy exit... If we are just trying to minimize as many zeros as possible and hope that most are at the two to three times Moic, that is a very successful venture capital firm.” — Troy [56:09]

• Trends Observed:

  • Lots of emerging funds in 2020–21; many have since closed.
  • Competition, fund size, and the risk profiles across asset classes discussed.

9. Career and Life Advice

Timestamp: [58:32] – [58:59]

• Troy’s succinct advice:

  “Just be risk on. That's kind of one thing I've always learned either on yourself [or the] work that you're doing. Right. … More often than not they took risk in their life and made something of it.” — Troy [58:32]

Notable Quotes

• “Sometimes you have that dog in you and sometimes you don’t. If you don’t, you can grow it.” — Troy [17:49]
• “At the end of the day, you can be very good at all the LBO, Excel work and PowerPoint stuff, but you have to be a pretty chill person for people to like you.” — Troy [36:38]
• “I decided to just cut bait because I figured the juice was not worth the squeeze there.” — Troy [12:57]
• "Don’t listen to the haters. LinkedIn Easy Apply is a way that a lot of people get jobs these days." — Troy [14:04]
• “If we want to have longevity in this world, this fund one has to go well… we're definitely not playing the power law…” — Troy [57:23]

Key Takeaways

• Unconventional backgrounds can lead to top finance roles, especially when combined with grit, disciplined execution, and smart strategies (like community college transfers).
• Personal fit and culture are as important as technical skills in banking and PE.
• The New York venture scene, embodied by Connexa, is marked by rigorous, quantitative analysis, strong fundamentals, and down-market diligence, in contrast to more hype or ‘vibe’-driven approaches.
• Aspiring investors and analysts should prioritize deep reps and continuous learning, starting with the basics (and lots of YouTube!).
• Taking thoughtful risks—on yourself and your work—is essential for outsized success.

This summary delivers rich context and concrete insight from the episode for anyone interested in private equity, venture, or the inside track to institutional investing.