How to Actually Raise Debt and Equity to Buy a Business
Most of what's written about buying a business assumes you already have the capital to close. Fellow investor Michael Trachtenberg at Cedar Elm Capital wrote a guide that fills that gap - and it's one of the more thorough, practical resources I've seen on the topic. The guide covers the full raise process for deals in the $2M to $10M EBITDA range: how to structure the capital stack, who the lenders and investors are, how to build your outreach list, what goes in the investor presentation, and how to get from term sheets to wire. It's written for acquisition entrepreneurs, business owners doing add-ons, and management teams doing buyouts. I definitely second Michael's point that money isn't the constraint in this market - quality opportunities brought by credible buyers are. And his framing that a professional process is the one thing entirely within your control is spot on. I'd add two things from our experience at Entrepreneurial Capital: get your capital relationships in place as soon as you can - knowing who is on your cap table can be immensely helpful in getting to that signed LOI - and never put anything in an LOI you can't actually finance. Both of those mistakes are more common than they should be. Partner Perspective: Chat Joglekar, Baton: Why 3 in 4 Buyer Conversations Go Nowhere We just analyzed six months of buyer activity on Baton, covering more than 12,000 buyer actions across 1,500+ businesses. One number varies more than any other in the data. Out of every 100 buyers who request an introduction to a seller, how many go on to make an offer? The platform average is roughly one in four, but the pattern differs across industries: In business support services, more than four out of five introductions lead to an offer. In media and software, roughly one in eight. The category where introductions most often become offers is also the one where buyers send the fewest introduction requests. Business support services generate fewer of them than almost any other category we track. The buyers there do their homework before reaching out, so by the time they request an introduction, they have mostly already decided. Fewer conversations, but better ones. Software is the mirror image. It draws heavy attention and premium asking prices, and then five out of six conversations go nowhere. In categories like that, most of the buyers you're competing against are window shopping. The pattern behind the discrepancy is how much homework a category requires. With a staffing agency, the listing shows buyers almost everything they need to decide, so they ask for an introduction only when they're close to making an offer. With a software business, buyers can't judge the risks until they talk to the owner, so they ask for introductions much earlier, while they're still deciding. Our advice: If you're searching, finish your homework before you request the introduction. Buyers who reach out with financing mapped, experience framed, and questions ready are competing against a field where three conversations out of four go nowhere. In this market, being qualified before you reach out is the whole edge. This is just one takeaway from ten industries’ worth of buyer data, from median asking prices to how often interest turns into an offer. Read the full report here. After The Acquisition: Introducing WithCoverage This month's After the Acquisition partner is one that's relevant both before and after you close: WithCoverage, a risk management firm built specifically for small and mid-size business owners. Here's something that catches a lot of first-time buyers off guard: insurance is often one of the biggest line items in a trades or services business. HVAC, landscaping, and similar companies can spend six figures annually on coverage - and most of that spend is being managed by a generalist broker who doesn't specialize in your industry, your risk profile, or your growth plans. WithCoverage takes a different approach. They partner with you as a team of insurance experts, attorneys, and claims specialists who specialize in your exact type of business. Their in-house risk attorneys are included at no extra cost, and their AI platform allows them to analyze and compare policies in ways that most brokers simply can't. The result is better coverage, better advice, and in most cases, meaningful savings. They also offer pre-close risk diligence and risk transition analysis, which makes them relevant for searchers still in the deal process as well as operators who are already running a business. If you're acquiring a business and want to understand what you're walking into on the insurance side before you sign an APA, that's a conversation worth having early. WithCoverage is a particularly strong fit if your business spends more than $100K annually on insurance, has revenue over $5M to $10M, or if you're planning to acquire more than one business per year. We're excited to have WithCoverage as a monthly contributor for After the Acquisition - expect practical guidance on risk, insurance, and protecting what you're building. Phil Wilusz - Head of Claims at WithCoverage: The Claim That Can Follow You Through Closing When you acquire a business via a stock purchase, its open insurance claims don’t disappear at closing. If no one manages the handoff, these claims can get lost between the seller, the new owner, the broker, and the insurance carrier. Imagine taking ownership on Monday and learning a week later that an employee injury claim is still open. The seller thought the broker was handling it, but the broker is waiting for documents. The carrier still has money reserved against the claim, but no one told them the business changed hands. A problem that started before you owned the company is competing for your attention while you’re trying to learn the operation, meet employees, and manage cash. That’s why WithCoverage takes control of the claims handoff before ownership changes. We determine what happened, what has been paid, what remains unresolved, and who is responsible for moving each claim forward. We help get older claims closed, but when a claim needs to remain open, we make sure the responsibilities and next steps are clear. With everything organized in one simple platform, WithCoverage lets you see your claims, policies, and coverage without digging through PDFs or old email threads. The result is a cleaner handoff, fewer surprises, and one less part of the business to manage as you step into ownership. Plus: We've spoken to a lot of searchers who are interested in working with a partner, but don't know where to look. If that sounds like you, feel free to complete this form. We’ll expose the results next week, and hope to make this a living directory for finding exceptional search partners.redacted