The Relationship First Sponsor

Cesar Herrera, Vice President at Mako Capital, joins Matt on Relationship First Sponsor to talk about his path from Columbia and investment banking to Blackstone, the AI-enabled roll-up venture he started, and what he’s learned about building relationships.They cover how to stand out when recruiting for top-tier finance roles, why endurance sports and discipline matter at work, and how Mako approaches healthcare, insurance and essential services. Cesar shares how AI is changing deal work and where he thinks teams over-automate. They also discuss building a network on LinkedIn, keeping it active with a CRM, the shift from independent sponsor to a funded fund, and choosing aligned LPs.The episode closes with a rapid-fire round: a book recommendation (Essentialism), relationship-building advice, and lower middle market firms worth watching.Topics: lower middle market private equity, independent sponsors, AI in private equity, relationship building, LP alignment, bootstrapping vs. raising capital.Guest: Cesar Herrera, Mako CapitalHost: Matt, Relationship First SponsorSpotify chapters (Spotify uses the same timestamps in the description)0:00 Highlights0:41 Welcome and guest introduction1:05 Cesar’s background2:39 What sets candidates apart in finance recruiting6:28 Sports, endurance and discipline11:30 Starting Calypso and joining Mako15:05 Mako’s investment thesis16:03 AI adoption and value creation24:16 A first-principles approach to AI28:45 Relationship-driven deal flow33:20 Keeping your network active with a CRM40:15 Independent sponsor model vs. raising a fund44:30 LP alignment49:55 Bootstrapping vs. outside capital54:45 Private equity vs. venture capital57:10 Rapid-fire round1:02:20 Wrap-up

What does it take to build a successful independent sponsor business, develop a strong deal pipeline, and use technology to work more efficiently?In this episode of The Relationship First Sponsor, Matthew speaks with David Acharya, founder of Acharya Capital Partners, about his experience in investment banking, private equity and independent sponsorship.David discusses the challenges of investing without committed capital, the importance of financial runway, and the relationship-building skills required to source deals and attract investors. He explains how he designed a Salesforce-based CRM around the needs of his firm, why capturing relationship history matters, and how automation and AI could reduce administrative work and help investment teams focus on finding and executing deals.The conversation also covers lessons from a major investment success, managing debt conservatively, developing strong management teams, maintaining company culture and making difficult leadership decisions.Whether you're an independent sponsor, private equity professional, entrepreneur or business leader interested in AI and business process automation, this episode offers practical insights into relationships, investment strategy and building more efficient businesses.Topics include:Independent sponsorship and private equity investingDeal sourcing and investor relationshipsCRM systems and relationship intelligenceAI, automation and more efficient business workflowsInvestment discipline, leadership and company cultureNetworking and the long-term value of professional relationshipsHosted by Matthew on The Relationship First Sponsor, a podcast exploring the relationships, strategies and decisions behind successful dealmaking.

Ridwan Rashid of BP Energy Partners joins Relationship First Sponsor to explain how a one-person deal team uses an AI agent to source deals, and how that agent has doubled his response rate for about $200-300 a month.He covers his path from city government to IBM to Cantor Fitzgerald to private equity, how he set the agent up in about five months, and why data providers now charge twice for the same tools once you want API access. He also talks about how AI is narrowing the gap between lower middle market firms and mega funds, what young analysts need to stay valuable, how it plays with LPs, and why some portfolio companies embrace AI while others hold back.Topics: AI in private equity, deal origination, AI agent costs, energy investing, PE careers, and rapid-fire reading picks.#PrivateEquity #AIAgents #LowerMiddleMarket #DealSourcing #IndependentSponsor

Most independent sponsors will lose, and the math explains why. Ian Reynolds, founder of Thesis Capital, joins us to talk about buying and running lower middle-market businesses.We talk about why operator experience beats financial engineering, how his team uses AI to rebuild costly software and cut costs, and why talent is the real moat in small businesses. Ian also covers free cash flow vs. EBITDA, how fee drag erodes LP returns, and what first-time independent sponsors should consider before starting.You'll learn:- Why operators outperform pure finance backgrounds- How AI changes the build-vs-buy decision for software- Which sectors Thesis avoids, and why- The numbers behind the independent sponsor boom: 328,000 businesses, 40,000 buyers- How to raise capital and choose the right investorsIan also shares what he's reading and how he stays informed.Not investment advice.