Why Buying a Business is More Like Dating Than Shopping

Be a savvy buyer

Here’s a tip: 

When looking for a business to acquire, stop thinking that the sellers will sell to you just because you have the finances or lending to complete the deal. 

If you don’t have relevant experience, or are asking the seller or broker irrelevant questions, don’t get frustrated when they tell you that you aren’t a good fit for the business. It’s because…

Buying a business is more like dating than shopping.

Joey Tribbiani Flirt GIF

Too many times, I’ve seen first-time buyers think they can approach business acquisitions like a retail transaction: see something you like, pay the asking price, and walk away with your purchase. But buying a business is far more nuanced and personal – it's more akin to dating than shopping.

For many business owners, their company represents years of dedication and emotional investment. It's their life's work and legacy. This deep personal connection means that selling isn't just about getting the highest bid; it's about ensuring their creation continues to thrive after they step away.

Consider a successful digital business that's been carefully built over the years. The owner has nurtured relationships with customers, developed unique processes, and created a distinct company culture. When selling such a business, they're not just transferring assets – they're entrusting someone with preserving and growing something deeply personal.

This emotional investment means owners often look well beyond financial capabilities when evaluating potential buyers. They want to know:

  • Do they have the vision and experience to guide the business successfully?

  • Will this buyer continue to employ our team?

  • Are they genuinely passionate about our industry?

Smart buyers recognize this dynamic and approach acquisitions with empathy and understanding. They:

  • Demonstrate their capability as future stewards of the business

  • Take time to learn about the company and what makes it special

  • Share their vision while respecting the company's existing legacy

  • Build rapport through honest, transparent communication

Don’t forget, many deals include some seller financing. What do you bring to the table to encourage the seller to lend you 6 or 7 figures? Do you think they are going to do that if you don’t have any relevant experience and this is your first shot at running a business? Doubtful. It takes two to tango- the buyer should be just as reliable as the business. 

Successful acquisitions come from buyers who position themselves not just as purchasers, but as educated and worthy successors. They understand they're not just buying assets and cash flow – they're being entrusted with something precious that represents years of hard work and dedication.

tango GIF

“Successful acquisitions come from buyers who position themselves not just as purchasers, but as educated and worthy successors.”

Business Acquisition Preparation Guide

Professional Presence

  • Maintain a complete LinkedIn profile with professional photo and clear acquisition goals

  • Audit social media for professionalism

  • Consider creating a dedicated website outlining your background and objectives

Financial Preparation

  • SBA Financing: Gather documentation and seek pre-approval (10% down, 10-year terms)

  • Maintain updated personal financial statement (SBA Form 413)

  • Monitor and improve credit score during the process

Industry Knowledge

  • Study relevant business models (SaaS, e-commerce, content sites)

  • Learn key metrics (CAC, LTV, churn rate, ROAS)

  • Stay current through industry newsletters and events

Professional Communication

  • Prepare a concise elevator pitch about your background and goals

  • Show genuine interest in sellers' stories and motivations

  • Maintain punctuality and transparency throughout the process

  • Communicate professionally in all interactions

Due Diligence Questions

  • Financial: Revenue streams, acquisition costs, historical performance

  • Operations: Systems, owner involvement, essential tools

  • Growth: Scaling challenges, industry trends, expansion opportunities

  • Team: Structure, key personnel, post-acquisition retention

Confidentiality

  • Read and strictly follow NDAs

  • Never contact sellers directly without broker approval

Deal Structure

  • Research industry-standard multiples

  • Prepare for 10-30% down payment

  • Present professional written offers (LOI)

  • Approach negotiations with a win-win mindset

  • Focus on creative problem-solving when issues arise

Remember: Like dating, the more attractive the business, the more selective the seller can be. Approach the process with this mindset, and you'll find sellers much more receptive to your outreach. 

Tips, tactics and value delivered to your inbox:

Subscribe and Gain Access

Hit the subscribe button below to gain access to all supporting documents, templates and spreadsheets I’ve shared so far in previous newsletters (and more) to help you in your online acquisition and growth journey.

Subscribe Below to Gain Access

Subscribe to keep reading

This content is free, but you must be subscribed to Digital Acquisition Club to continue reading.

Already a subscriber?Sign In.Not now