0028 - A 25-Year Employee's Path to Ownership: Overpaying on Purpose Using None Of His Own Money

In this episode, Tim talks with Mike Webster, an operator-turned-owner who spent years working inside a company before eventually buying it himself. Mike shares how his time as an employee shaped his understanding of the business, what he saw behind the scenes that made him consider ownership, and the complicated emotions that come with transitioning from worker to buyer.

He also opens up about evaluating whether growth is worth the cost, dealing with burnout, and the mindset shift required to separate personal identity from the business you run.

Tim is an entrepreneur who believes everyone should explore the opportunities that business and real estate can provide on the path to financial freedom. He owns and operates a wine & liquor store, a software startup, a consulting company, and a growing portfolio of commercial and residential real estate.

Tim's passion for independent business has led him to support dozens of other business owners. For over a decade, he has worked with businesses on strategy, processes, finances, and marketing. These experiences, along with analyzing dozens of other businesses for potential acquisition, have provided Tim with an immense knowledge base to pull from.

Tim has appeared on multiple top-tier podcasts in the financial space, such as Bigger Pockets Money and The Freedom Chasers Podcast.

[00:00 – 12:30] The Growth Dilemma & Becoming a Key Operator

Mike explains the contradiction of growing the business even though it would raise the price he'd eventually have to pay for it, and how he became the de facto operator running the company day to day.

[12:31 – 25:00] Early Career, Sales, and Learning the Business

Mike shares how he got into the industry, his early sales experience, the mentors who pushed him forward, and how he learned the operational side from the inside.

[25:01 – 38:00] Friction With the Owner & Stepping Into Leadership

How responsibilities shifted as the business grew, the strain of carrying more weight without ownership benefits, and the point where Mike realized he needed to make a move.

[38:01 – 52:00] Preparing for a Buyout & Understanding Real Valuation

Mike breaks down the moment he recognized he was effectively running the business, how he evaluated its value, and the internal debate over whether growth was worth it.

[52:01 – End] Burnout, Identity, and Deciding What Comes Next

What Mike learned about separating himself emotionally from the business, avoiding burnout, and how he approached the decision of whether to buy the company he helped run.

Guest Bio
Mike Webster is an experienced operator who deeply understands the challenges of running and scaling a business from the inside. After years of managing day-to-day operations, he began evaluating whether purchasing the company he worked for made strategic and personal sense. His journey highlights the realities of growth, burnout, valuation, and the mindset shifts required when transitioning from employee to prospective owner.

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Tweetable Quotes:

"Am I really going to grow something… just so I can pay more for it?" – Mike Webster

"You can't let the business define who you are — that's when everything starts feeling heavier than it should." – Mike Webster

"Sometimes the best decision isn't scaling — it's stepping back to understand what you actually want." – Mike Webster