Podcast artwork thumbnail for Own The Exit

Own The Exit

Caleb Edwards, Aaron Leatherdale

Booking Overview

This is an entrepreneurial finance and investment podcast focused on business exits, passive income, and wealth preservation, combining host-led educational episodes with occasional interviews of alternative investment professionals. Credible pitches include founders who have completed successful exits, fund managers, real estate and private-market investors, and experts in post-liquidity wealth strategy; booking difficulty is medium because the show has featured a high-level alternative investment strategist but appears selective and interview-led only occasionally.

Metrics

Episodes: 153

Frequency: Weekly

Rating: 4.9/5.0

Estimated listeners: 1k-10k

Gender skew: Male

Location: USA

YouTube: 1.1k subscribers

Instagram: 1.1k followers

Contact Information

Publicly listed emails

caleb@oakiq.com

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Host

Caleb Edwards - Entrepreneur and investment-focused podcast host covering business exits, passive investing, real estate, alternative assets, and durable wealth creation.

Aaron Leatherdale - Investment-focused podcast host discussing liquidity events, capital deployment, passive income, real estate investing, and fund structures for entrepreneurs and investors.

Booking Intelligence

Booking Requirements

medium
Typical Credentials:  
Founders with meaningful business or investment experience, alternative investment strategists, fund managers, real estate operators, and specialists in wealth planning after a liquidity event. Strong candidates should offer firsthand experience with exits, passive-income strategies, private markets, multifamily real estate, or differentiated alternative assets.
Required Achievements:  
Successful business or investment exits, Raised substantial venture or private capital, Founded or led an investment firm, Built expertise in multifamily real estate or alternative assets, Demonstrated experience helping entrepreneurs achieve financial independence

Recent Guest Discussions

Morgan Keim - Entrepreneurial Burnout, Passive Income, Multifamily Real Estate, Workforce Housing, Conservative Underwriting, And Niche Alternative Investments.

Recent Topics

Business Exits, Alternative Investments, Real Estate, Wealth Building, Entrepreneurship

Episodes

Here's the recent few episodes on
Own The Exit
:

Why High Earners Are Looking Beyond Traditional Financial Advice

September 08, 2026

What happens when your income has outgrown the way you invest? In this episode of Own The Exit, Caleb and Aaron sit down with Ben Oberg of The Capitalist Network to unpack what high-income accredited investors are actually prioritizing as they move beyond traditional financial strategies and take greater ownership of their wealth.From oil and its tax advantages to cash-flowing real estate, development deals, and institutional-grade assets, the conversation reveals why every investment doesn't...

This Vacant Building Became a 4X Deal

September 01, 2026

Most investors are out hunting for “good deals”… but what if the real money isn’t found—it’s created? In this episode, we take you inside a real project that sat vacant for three years and show how it was transformed into a high-performing asset with multiple income streams.We walk through the full evolution of this building—from an outdated medical office with heavy restrictions to a thriving co-working hub, studio, and community space. This is a masterclass in seeing opportunity where other...

Why We Bought Negative Cash Flow

August 25, 2026

Most investors are chasing cash flow and appreciation… but what if those aren’t actually where your returns come from? In this episode, we break down the real drivers behind profitable real estate investing—and why focusing on surface-level metrics can quietly cost you millions.We walk through two real deals: one that had negative cash flow on day one but delivered massive upside, and another that looked “safe” with nearly 6% cash flow—but was actually projected to lose money. If you’ve ever ...

Publicly listed emails

caleb@oakiq.com

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