When founders need capital to grow, giving away equity can seem like the obvious solution—but it may also mean giving up a valuable piece of the company they’ve worked so hard to build. Understanding when to use debt instead of equity can help entrepreneurs fund growth while preserving ownership, control, and more of the upside when they eventually exit.
In this episode of Build It to Billions, Brett Swarts sits down with James Mendelsohn, Founder and Managing Director of Proximo Capital, to explore how entrepreneurs can think strategically about raising capital. They discuss debt versus equity, what lenders look for, financing growth and acquisitions, and how founders can build a stronger capital strategy without unnecessarily diluting their ownership.
Episode Highlights Here:
Intro
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Brett
Welcome to the Build Up to Billions podcast, where we guide successful entrepreneurs and investors on their journey from millions to billions. We believe the key to scaling and compounding your wealth in life starts every single day with the mindset and practice of stewardship over ownership and applying billionaire biblical principles. Our ultimate goals have to scale and compound your wealth in life, so you give more all the way to help MVPs. My name is Brett Swartz. Each and every episode, we’re joined by the world’s top entrepreneurs, investors, and millionaires or billionaires, and they share their secrets, insights, and wisdom with us, so we can all level up and make a bigger impact. We’re also sharing on CapitalGainsTaxSolutes.com as well for anyone who has a large exit of Bitcoin business, real estate, and wanting to eliminate the need for the 1031 exchange and build a capital gains tax or estate tax exit plan, just go to capitalgainstaxolutions.com. I’m excited about our next guest. He’s out of Virginia, and he is on a mission to help bring capital to mostly businesses with five to $50 million of revenue, or in that range, and he is an experienced leader and operator in financial services, and he is focused on lending and payments with specialty and raising debt and equity capital for clients in diverse industries and growth stages of growth. He’s worked with both large and small companies on capital optimization, go-to-market strategy, product and geographic expansion, and mergers and acquisitions, and he has had leadership roles at several firms, including Capital One, where he was a vice president of corporate strategy, Can Capital, where he’s a chief marketing and sales officer, and so much more. Please welcome the show with me, James Mendelson. James, how we doing?
James
We’re doing great. Thanks for having me on the show.
Brett
Excellent. For our listeners get to know you for the first time, would you share us a little bit more about your story and your current focus?
James
Yeah, I’m originally trained as a statistician. Started working at Capital One. I often joke back when we were trying to figure out how to sell people credit cards, but did a lot of work in card marketing, risk management, and corporate strategy. Then I was at the McKinsey consulting firm, and I spent five years as an operating partner in private equity, doing merchant lending and asset management. And when I got out of PE, I really focused on advising balance sheet lenders and on strategy and go to market, and what they needed a lot more help raising capital, and so starting about eight years ago, I really started focusing on raising debt and equity capital. Initially in lender finance, and then over time we’ve expanded. So, we do a lot of work in in real estate, government contracting, renewable energy, a lot of other verticals, raising both debt and equity, and doing M and A advisory work and M and A transaction finance.
Brett
Excellent, fantastic. And given the current marketplace as it pertains to lending for businesses, what’s kind of the number one thing that you’re seeing and that you’re filling the gap for capital?
James
Yeah, I mean, I think the number one thing is still is still true over the long tall, which is it’salways harder for smaller firms to get access to the capital markets, and so part of what we
focus on trying to democratize access to those sources of capital, and the more constrained banks get with lending limits, concentration limits, other kind of underwriting requirements, the more private credit looks attractive. And right now, there’s a ton of available supply of capital in the private markets. I think the other thing that’s happening now is much more focus on not just the traditional financial discipline, but also how to manage operational risk.
Brett
Okay, that makes sense. And when it comes to businesses that are expanding right now and/orneeding capital, AI perhaps is playing a role in this. And or what do you what are you seeinghow that’s changing the way that companies are expanding, and/or the need for capital.
James
I think I always like the analogy that we’re sort of in the top of the first inning of AI. I think you know the first impact on business operations is a lot of really, I think impactful automation, the some of the reduction in expense. I think things around, you know, marketing acquisition, back-office operations, things like that have gotten much more efficient very quickly by leveraging AI tools. I think from a growth stand. Point that is, I’ll say two things from a capital perspective. I think for a any company who is beginning to use AI well, I think becomes a more attractive candidate for investment capital.
Brett
So, if you like this little short clip of the interview I just did, click over here to watch the full interview, and please don’t forget to subscribe. Thanks so much, everybody
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About James Mendelsohn
James Mendelsohn is the Founder and Managing Director of Proximo Capital, a boutique investment banking and capital advisory firm that helps growing companies access debt, equity, and strategic financing solutions. He brings extensive experience across corporate finance, lending, payments, M&A, and growth strategy, helping business owners navigate capital decisions while positioning their companies for long-term growth.
Before founding Proximo Capital, James held senior leadership roles at Capital One and CAN Capital and worked with McKinsey & Company, advising organizations across financial services and other industries. He earned his BS in Economics from the Wharton School and his MBA from the University of Maryland. Today, James works with entrepreneurs and companies on capital raising, acquisition financing, real estate financing, and other strategic transactions.
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