0032 - Why a $280K Fashion Brand Looked Like a Great Deal… Until It Didn't
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In this episode, Tim talks with Milan Nolen, an entrepreneur and business buyer who shares a transparent look at evaluating risk, recognizing red flags, and knowing when not to do a deal. Milan walks through her transition from employee to founder mindset, the early mistakes she made by moving too quickly, and the moments that forced her to slow down and reassess what she was really buying.
She explains how ignoring basic math and operational realities nearly pulled her into a bad acquisition, why non-operating businesses carry hidden danger, and how learning to walk away became one of the most valuable skills she developed as a buyer.
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 – 08:20] From Employee to FounderMilan describes the mindset shift required to move from employee thinking to ownership, and why she didn't fully grasp that transition until she was already deep into the process.
[08:21 – 16:20] Early Assumptions & Missed MathHow moving too fast, skipping the numbers, and relying on optimism created blind spots that could have led to a costly mistake.
[16:21 – 24:00] Red Flags & Reality ChecksMilan breaks down the moment she realized the deal might be a "dumpster fire," and how recognizing operational and structural issues changed her approach.
[24:01 – 36:30] Non-Operating Business RiskWhy buying a business that isn't actively operating introduces a completely different risk profile — and why that realization became a turning point.
[36:31 – 49:00] Knowing When to Walk AwayThe emotional and strategic challenge of stepping back from a deal, even when the desire to buy is strong.
[49:01 – End] Lessons for First-Time BuyersMilan's key takeaways for buyers evaluating their first acquisition, including patience, discipline, and respecting what the numbers are telling you.
Guest BioMilan Nolen is an entrepreneur and business buyer who focuses on disciplined deal evaluation, risk awareness, and long-term sustainability. Through her experience navigating potential acquisitions, she emphasizes the importance of math, operational clarity, and the confidence to walk away from deals that don't make sense.
If you found value in today's show, make sure to subscribe so you never miss an episode packed with insights to help you buy and grow a business that creates real financial freedom.
Connect with Milan:Instagram: @milanterez
TikTok: @milanterez
Website: milantereznolen.com
Website: https://www.powerofbiz.com
YouTube: https://www.youtube.com/@powerofbiz
Instagram: https://www.instagram.com/timtdelaney/
Threads: https://www.threads.com/@timtdelaney
LinkedIn: https://www.linkedin.com/in/timothytdelaney/
Facebook: https://www.facebook.com/timtdelaney
"Either this is a complete dumpster fire, or there's a deeper reason here." – Milan
"I still want to buy a business — I just don't think this is the one to do it with." – Milan
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