Inside Institutional Investing W/Kris Benson
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Episode Description
Welcome to the On The Rise Podcast! In this episode, Jeremy Dyer sits down with Kris Benson, Partner at Blue Line Ventures and former Chief Investment Officer at Reliant Real Estate Management, to explore how long-term tailwinds drive outsized investment success. Kris shares his journey from sales and medical devices into institutional real estate, self storage, and now private equity focused on acquiring niche B2B service businesses. The conversation breaks down why small business M and A is one of the most compelling opportunities today, how institutional capital really evaluates deals, and why alignment matters more than headlines. Kris also offers a thoughtful perspective on asset class cycles, operator selection, and how investors should think about diversification beyond Wall Street. This episode is a must-listen for investors seeking durable wealth through Main Street opportunities.
Summary
Tip 1: Tailwinds Matter More Than Timing
“If there are tailwinds behind you, you can screw up a lot of stuff and it’ll still work out.”
Kris frames his entire investment philosophy around long-term demographic and economic forces rather than short-term market timing.
Tip 2: Freedom Beats Income
“It’s not making more money, it’s freedom of time.”
Leaving a high-paying medical device career taught Kris that time flexibility, not salary, defines real success.
Tip 3: Institutional Scale Changes the Game
“When you understand the partner’s horizon, everything becomes clearer.”
Institutional capital is not monolithic. Understanding incentives, hold periods, and alignment is critical to successful partnerships.
Tip 4: Shiny Asset Classes Create Risk
“When everyone is talking about it, it’s probably time to be careful.”
Kris cautions against chasing hype-driven asset classes and encourages investors to evaluate where each asset sits in its cycle.
Tip 5: Private Markets Reward Patience
“These are illiquid investments for a reason.”
Longer hold periods and reduced liquidity are often the tradeoffs that generate excess returns in private investments.
Tip 6: Small Businesses Are America’s Backbone
“This is America.”
Kris shares how acquiring multigenerational businesses is not just financially compelling, but deeply meaningful.
Tip 7: Quality Always Comes First
“Do they wake up thinking about the customer?”
Whether the owner stays or exits, product and service quality define long-term value.
Tip 8: Operators Are Still the Jockey
“You’re buying the reputation of the business.”
Even great businesses fail without the right leadership structure and support.
Tip 9: Alternatives Are Gaining Ground
“There’s a lot of alpha to be had.”
Kris explains why alternatives are becoming a core allocation for sophisticated investors.
Resources and Links
Website
https://www.blueline-ventures.com
Social Media
LinkedIn: Kris Benson
