Mastering Online Business Acquisitions and Exits at Flippa University with Ben Zogby

In this episode of Humans of Flippa, Ben Zogby, entrepreneur with a $1.8M exit, business acquirer, and founder of Flippa University, shares his experience and insights from both selling and buying businesses on Flippa.

In this video, Ben offers a unique perspective from both sides of the transaction and provides practical guidance on preparing for success, avoiding common pitfalls, and structuring deals that benefit all parties, and how Flippa University can help prepare you for that successful exit or acquisition.

Making It Easy to Sell Online Businesses
Flippa provides owners and investors with the tools and expertise to sell.

400,000+ Weekly Active Buyers

15 In-house Brokers and 120 Broker Partners

Negotiate and Receive Offers Fast

Integrated Legal, Insurance and Payments

Ben’s Journey From 7-Figure Seller to Educator

Ben’s journey began in 2018 when he launched Highstrike while working his engineering job. Over the next five years, he scaled it into a seven-figure business before successfully exiting on Flippa in 2023. Since then, he’s made digital M&A his career, having experienced both sides of the marketplace as a seller and buyer.

“Digital M&A in general, but specifically digital M&A has really become a popular career now, especially over the last five years,” Ben explains. “A lot of people are coming to the buyer table or seller table with not too much experience and kind of not really knowing what they’re doing.”

This knowledge gap inspired him to create Flippa University, a comprehensive educational platform designed to help business owners prepare for successful exits and guide buyers through the complex acquisition process.

Three Critical Areas for Owners Looking to Exit

Ben emphasizes three critical areas that business owners must address when preparing for an exit:

1. Removing Owner Dependency

“The biggest common problem that I see when sellers want to sell a business is that they are the business,” Ben notes. When the owner is integral to day-to-day operations, the business becomes less valuable to potential buyers.

This was a particular challenge for Ben with Highstrike, where he was initially the face of the brand. The process of working himself out of the business took nearly two years—a considerable investment of time that dramatically increased the business’s value to acquirers.

“If you are the business and you get removed, then unfortunately your business is worth zero. And it’s not really a business, it’s a job,” he explains. Creating systems, documenting processes, and hiring team members to handle responsibilities previously managed by the owner are essential steps in this transition.

2. Patience Throughout the Process

Selling a business is rarely quick, particularly for larger operations. Ben likens the exit process to an iceberg: the actual transaction represents just the visible tip, while the preparation work constitutes the massive structure below the surface.

“If you’re coming to the seller’s table thinking you’re going to get a deal done in 30 days, it’s one of two things that’s going to happen,” warns Ben. “You’re going to burn yourself out…or you’re going to settle for a deal that really doesn’t make a ton of sense for you because it’s rushed.”

In Ben’s experience, while the actual transaction took about seven months, the preparation—including working himself out of the business—required two years. Though not every business will need that much time, rushing the process almost always leads to suboptimal outcomes.

3. Building a Business That Will Last

Perhaps most importantly, Ben advises business owners to “act like you’re going to own the business forever.” The fundamentals that make a business sustainable, scalable, and profitable are precisely the same qualities that make it attractive to buyers.

This includes maintaining clean financial records from the beginning, tracking key metrics like customer acquisition costs and lifetime value, documenting systems and processes, and solving operational problems before they become barriers to a sale.

“Owning the business forever comes down to doing all the things that you would want your past self to have done if you were to buy the business yourself,” Ben explains. This mindset ensures that the business is always in a state of readiness, whether an exit is imminent or years away.

Strategic Insights for Buyers

For those looking to acquire an online business, Ben shares four essential principles based on his experience:

1. Take a Systematic Approach to Finding Opportunities

“Expect to look at a thousand businesses before actually buying one. Expect to have a hundred conversations before buying one business,” Ben advises. This methodical approach allows buyers to develop context, compare opportunities, and identify truly exceptional deals.

Ben’s personal process involves checking Flippa daily, filtering by the most recent listings to ensure he doesn’t miss new opportunities. This disciplined approach helps him maintain a large sample size of potential deals, making it easier to recognize standout businesses when they appear.

2. Always Be Willing to Walk Away

During negotiations, maintaining the ability to walk away from a deal is crucial leverage. “If you’re not willing to walk away if the terms get unfavorable, then you’re really in a vulnerable position,” Ben notes.

He suggests that the best deals often leave both parties slightly unsatisfied—sellers feeling they could have received more, and buyers feeling they paid slightly too much. This indicates a balanced negotiation where neither party dominated the process.

3. Analyze Risk vs. Reward Carefully

Ben’s investment philosophy centers on placing “small bets to win big.” He looks for opportunities with limited downside risk but substantial upside potential. This approach is particularly important for first-time buyers, who might be tempted to pursue larger deals without fully understanding the associated risks.

“If the pessimistic scenario plays out, what is the worst case scenario here?” Ben asks. “And if that worst case scenario is like, I lose 20 grand, then that’s, and the upside is I make a couple million, then that’s great.”

4. Have a Clear Post-Acquisition Plan

Before finalizing any deal, buyers should have a concrete plan for their first steps after taking ownership. “Always know what your first 10 moves are or first 10 attempts are after buying the business,” Ben recommends.

Ben’s approach involves identifying a business’s weaknesses that can be transformed into strengths. For example, a successful business with a poor website presents an opportunity—improving the website could substantially increase performance with relatively little effort.

Developing Your Investment Thesis

Central to Ben’s buying strategy is having a clear investment thesis—a defined set of criteria that guide acquisition decisions. Without this framework, buyers risk becoming overwhelmed by the thousands of listings available.

“Without an investment thesis, you’re basically walking into a candy shop with no idea of what you’re gonna buy and everything’s gonna look appealing,” Ben explains. His personal thesis focuses on software and e-commerce businesses between $30,000 and $100,000, which he considers manageable risks with significant upside potential.

For new buyers without experience, Ben recommends starting small: “Buy something small, like really small and just figure it out.” A business generating even modest revenue provides invaluable hands-on experience that no amount of theoretical knowledge can replace.

Flippa University: A Comprehensive Learning Environment

Recognizing that courses alone often leave students with unanswered questions, Flippa University offers several components beyond standard instructional content:

• Weekly Workshops: Ben conducts separate sessions for buyers and sellers, providing feedback on specific deals and listings while answering questions in real-time.
• Community Support: Students connect with peers facing similar challenges, sharing insights and strategies.
• AI Assistant: An embedded AI tool helps students quickly find specific information without reviewing entire course modules.

“It’s a whole modern approach to learning,” Ben explains. “There’s the course, there’s workshops…if you don’t feel like going back to the course and trying to figure out where you heard a bit of information…you can just chat with the assistant.”

Enrolling in Flippa University

For those ready to begin their journey, Flippa University offers a seller’s course completely free of charge, while the buyer’s course is available for $299. Ben welcomes questions through LinkedIn and can be reached directly for additional information.

Whether you’re preparing to exit a business you’ve built from the ground up or looking to acquire a digital asset that aligns with your investment goals, Ben’s experience on both sides of these transactions provides valuable perspective for navigating the complex world of online business acquisitions.

By combining practical advice with ongoing support, Flippa University aims to help entrepreneurs make informed decisions throughout their business buying and selling journey—turning what is often a one-time life event into a repeatable, strategic process.

To learn the techniques and skills to acquire or sell like a pro, visit Flippa University here >

Questions?

For those interested in learning more about Flippa University, visit the Flippa University page, contact Flippa Support, or connect with Ben directly via his LinkedIn.

Making It Easy to Sell Online Businesses
Flippa provides owners and investors with the tools and expertise to sell.

400,000+ Weekly Active Buyers

15 In-house Brokers and 120 Broker Partners

Negotiate and Receive Offers Fast

Integrated Legal, Insurance and Payments