Acquiring in the Digital Space?

investor profile

September 08, 2025

by an investor from University of California, Berkeley - Haas School of Business in San Francisco, CA, USA

Acquiring in the digital space is quite different than acquiring a traditional business. There are many pitfalls and traps unique to digital businesses. Active platforms such as Flippa and Acquire are flooded with fly-by-night businesses that are low quality, built-to-sell businesses that have no value once the seller has sold and left the business. In fact, as an investor / searcher, this is the biggest obstacle that I face. 1) Do you generally acquire to run the business yourself? Or do you look for deals where the original owner and team are willing to stay on and run the business? These days sellers might also pretend to say they will stay on but how do you trust them once they cash out is a huge issue. 2) Do you hire competent people to help you run the business? And once you factor in the cost of installing a new CEO, the math may no longer work. In many cases, you are stuck with a full time job. But what if I want to be an investor and let someone else run the business? I would love to hear your story and thoughts.
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Reply by a professional
in Lucknow, Uttar Pradesh, India
I don’t buy fixer-uppers with previous owners still hanging around. I buy assets I can immediately plug into my existing money machine and start pulling cash. If the seller wants to “stay on,” that’s a dealbreaker. I want control. Total. No partners. No lingering exes. I only acquire when I’ve got leverage. If I’ve got a Facebook group of ecommerce folks? I’m buying that abandoned cart app. If I’ve got a course teaching how to turn content into recurring commission? I’m snapping up newsletters and side hustle communities. Sometimes I’ll even test the water by running ads in those assets before making a move. And right now, the asset I’m addicted to? Skool communities. They’re the only digital property I’ve found where I can cashflow in 24 hours flat. I run an auction or poll, and boom, money in. My playbook is simple: buy, plug into my ecosystem, get my money back fast, then hold long-term. I don’t hire employees. I train operators and give them a slice to run the show. I’m not buying businesses. I’m buying distribution, attention, and cashflow I can control. And the second I own it? It starts working for me, not the other way around.
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Reply by a searcher
from Cornell University in Dallas, TX, USA
In this area, I see digital platforms in the same way as other businesses: If you want to stay out of the day-to-day, the business must either (a) come with a strong mgmt team or (b) be large enough to afford one. Something to keep in mind is that the post-loan SDE needs to also pay for growth and/or operational investments, so the amount of available cash will dwindle quickly if you need to hire a GM or CEO.
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