About MBO Ventures
Darren's Story
Darren Gleeman started in quantitative finance. At Wharton he leaned into hard work, modeling, and the scientific method. After school he built a firm that automated trading, then transitioned it into one of the early fully automated quant hedge funds. That experience shaped how he approaches business decisions today, with clear goals, data, and simple rules that hold up under pressure.
He later moved from markets to Main Street, advising owners on succession, buyouts, and employee ownership. He founded MBO Ventures to combine two beliefs. First, that founders should not have to pick between a low-tax exit and a legacy they can be proud of. Second, that employees who share in the outcome treat the company like it is theirs, because it is.
Along the way, Darren has invested in and worked with companies across software, manufacturing, and services. He is especially active in industries that live with complexity, like cannabis, where rules and taxes can move the goalposts. His focus is the same in every case. Get owners a result they can defend, and set teams up to win.
What We Do
MBO Ventures is an ESOP advisor and investment partner. We design and execute transactions that let owners sell a portion or all of their company to an Employee Stock Ownership Plan, often with better after-tax outcomes than a typical private equity sale.
- We run the feasibility work so you know if an ESOP fits your goals
- We structure and finance the transaction, then stay involved after close
- We invest our own capital alongside owners and management when it helps the deal
Why ESOPs Are Powerful
An ESOP can be a practical way to sell while protecting people and brand. In many cases:
- No employee out-of-pocket cash is required
- Sellers may defer capital gains under Section 1042 if eligibility is met
- A 100 percent S corporation owned by an ESOP is generally exempt from federal income tax
- Principal on ESOP debt is repaid with pre-tax dollars
- Founders can stay in leadership and keep meaningful upside
- Employees become owners, which can improve engagement and retention
Every deal has rules, tax considerations, and fiduciary duties. We walk through those in plain English and coordinate with your legal and tax advisors.
When Owners Call Us
Family succession with one or more next-gen leaders in place
Management buyouts where the team wants real ownership
Full founder exit with a plan to protect culture and jobs
Rollovers and recapitalizations to de-risk while keeping upside
Cannabis ESOP Expertise
How We Work
We start with goals, numbers, and constraints. If an ESOP is not the right tool, we say so.
We model structure, financing, repurchase obligations, and governance. No surprises.
We coordinate lenders, trustees, valuations, and counsel. When helpful, we invest our own capital.
We stay involved on communications, board composition, and repurchase planning so the plan is healthy long term.
A Note From Darren
I have seen great companies sold in ways that left owners unhappy and teams out of the loop. There is a better way. If you want to explore an ESOP without hype, I will give you a straight answer, a clear model, and a path that respects the people who got you here.
A Note From Darren
I have seen great companies sold in ways that left owners unhappy and teams out of the loop. There is a better way. If you want to explore an ESOP without hype, I will give you a straight answer, a clear model, and a path that respects the people who got you here.
Impact We Aim For
Owners who exit with confidence about taxes, control, and legacy
Teams who understand what ownership means and how it grows
Companies that compete better because the people who power them have a real stake
Frequently Asked Questions About MBO Ventures
Lower middle market and mid-sized privately held companies where leadership wants a thoughtful exit and a durable plan for employees.
Often yes. With the right structure, founders can stay in management, retain board roles, and keep meaningful upside, while the ESOP owns the stock.
In a typical leveraged ESOP, employees do not pay out of pocket. The company funds the plan over time.
They can be. Section 1042 deferral, S corporation ESOP treatment, and deduction mechanics can improve after-tax results. Outcomes depend on eligibility and deal design. We model this clearly.