Buying and selling online businesses can be one of the most rewarding — or risky — moves an entrepreneur can make. Whether you're looking to acquire a content site, eCommerce store, or SaaS platform, real-world experience from seasoned professionals is invaluable.
We reached out to entrepreneurs, founders, and acquisition advisors to share their biggest lessons from online business transactions — from what to look for during due diligence to how to avoid costly mistakes.
Here’s what they had to say:
🧠 1. Patience Trumps Deal Desperation
Erik Daley, Founder & Co-Owner, Highest Offer
“Patience and discipline are the most critical factors for success. I’ve seen how ‘deal desperation’ leads even seasoned entrepreneurs to overlook fundamental flaws just to close a deal.
Saying no to mediocre opportunities is far more important than chasing a win. A poor investment won’t just drain finances — it can derail your entire business strategy.”
📌 Lesson: Don’t rush the deal. Wait for the right opportunity — not just any opportunity.
🔍 2. Go Beyond Surface Metrics
Phillip Young, CEO, Bird SEO Agency UK
“One of my best acquisitions was a content site with strong SEO but poor monetization. We improved conversion paths, added email capture, and diversified revenue through affiliates — profitability soared without needing much more traffic.
But I’ve also walked away from deals where all revenue came from one source — it’s just too risky.”
📌 Lesson: Look deeper than revenue or traffic. Assess customer retention, revenue diversity, and long-term stability.
📊 3. Always Verify Data Integrity
Eugene Mischenko, President, E-Commerce & Digital Marketing Association
“Years ago, I advised on acquiring a DTC brand. The numbers looked great — until we discovered that most sales came from unsustainable influencer discounts. We renegotiated based on realistic forecasts, saving the buyer from overpaying.
My advice? Validate everything: customer acquisition, retention, revenue sources, tech stack, and operations.”
📌 Lesson: Dig into the numbers. If they don’t hold up to scrutiny, neither will the business.
🚀 4. Focus on Market Fit and Scalability
Dhari Alabdulhadi, CTO and Founder, Ubuy Peru
“A successful acquisition involved a niche eCommerce site where we improved marketing strategy, leading to 150% revenue growth in a year. A failed one taught us the cost of hidden liabilities.
My advice: Transparency and communication are key. Clear expectations and trust make all the difference.”
📌 Lesson: Understand the business’s position in the market, and make sure both sides are transparent.
Final Takeaway
Whether you’re a first-time buyer or a seasoned seller, the consistent themes are clear: do your homework, be patient, and look beyond the headline numbers. These experts have been in the trenches — and their advice can help you avoid costly mistakes and make smarter deals.
