$25M Isn’t “Big-League” Money: The Private Deals You Can’t Access
Rob Anderson / Founder & CEO, Carlton Lane Capital
About this episode
You sold your company, paid your taxes, and put $25 million in the bank. You are not broke, but you are not in the big leagues either. That gap is exactly who Rob Anderson built Carlton Lane Capital for.
On the debut episode of The Private Equity Show, host Ryan Harper sits down with Rob Anderson, Founder and CEO of Carlton Lane Capital and a 27 year capital markets veteran, for a plain English masterclass on how private market investing actually works, and how middle ground investors, roughly $5M to $50M net worth, can finally access deals normally reserved for institutions and family offices.
After seven years running the capital arm of a Dallas real estate developer, Rob went independent in November 2025 to solve one problem: giving accredited investors institutional grade due diligence and access, without the conflicts of interest baked into most sponsor owned shops.
Inside this episode
- Public vs. private markets, explained simply
- Why the big firms (UBS, Blackstone, Apollo, KKR) structurally cannot offer you local, direct deals
- His buy box: recession resilient assets with an asymmetric risk and return profile
- Deep dives on medical office real estate, first lien lending, single family lot development, student housing, mineral rights, and oil and gas
- The tax playbook the ultra wealthy use: intangible drilling costs, Roth conversions at a discount, the passive 1031 exchange, Opportunity Zones (OZ 2.0), and bonus depreciation
- What he refuses to invest in, and why
- How AI is changing due diligence, and where it still cannot be trusted
Chapters
- 0:00Why $25M isn't "big-league" money
- 1:01What is private equity? Public vs. private markets
- 3:07Carlton Lane's pitch: the $5M to $50M middle ground
- 8:18Why he went independent (the conflict of interest)
- 13:20"Not a used-car salesman": third-party due diligence
- 14:34Using AI for diligence, and where it fails
- 24:45The buy box: recession-resilient + asymmetric risk/return
- 27:45Medical office & outpatient real estate
- 30:03First-lien lending / asset-backed private credit
- 31:10Single-family lot development (the contractual exit)
- 37:52Mineral rights & the Permian Basin
- 39:26Oil & gas drilling and the IDC tax break
- 44:38The UT Austin student housing deal
- 46:28Roth conversion at a discount
- 49:52What kills a deal at the finish line
- 51:19Emotion, M&A, and letting go
- 54:26Opportunity Zones (OZ 2.0)
- 57:07What he won't touch: assisted living
- 58:53Multifamily's comeback, market by market
- 1:01:16The passive 1031 exchange & bonus depreciation
- 1:03:16The hardest (and most fun) part of the job
- 1:04:45His ideal investor and developer partners
- 1:10:14The future of Carlton Lane
- 1:13:31Book recommendation: The Power of One More
From the taping
This interview is for informational and educational purposes only and is not investment, legal, or tax advice. Nothing here is an offer or solicitation to buy or sell any security. Private market investments are illiquid and carry risk of loss, including loss of principal, and are generally available only to accredited investors. Views expressed are those of the speakers. Figures cited by guests are their own and have not been independently verified. Do your own due diligence and consult your own advisors.