What I Learned From 200+ Buyer Conversations

I spent three years trying to sell Koio. Three years of calls, meetings, NDAs, LOIs that went nowhere, and deals that fell apart at the finish line. Along the way, I had over 200 conversations with potential buyers: strategic acquirers, private equity firms, family offices, search funds, and individual operators.

Most of those conversations went nowhere. Some felt promising for months before collapsing. A few got to the point where I thought we had a deal, only to watch it unravel in diligence.

We eventually found a partner who saw what we had built: the brand, the craftsmanship, the customer loyalty. They wanted to take it further.

Having been on both sides of M&A transactions (as an analyst at J.P. Morgan earlier in my career, and now as a Partner at Thunder VC where I work on deals), I've seen these patterns play out repeatedly. The lessons I learned selling Koio were hard-won, but they weren't unique. Here's what I know now that I wish someone had told me earlier.

1. The process takes 3-4x longer than you think

When I first started exploring a sale, I figured it would take 6-12 months. The reality was three years from "let's see what's out there" to signed purchase agreement.

Part of this was timing. The M&A market shifted dramatically during our process. Tariffs didn't help. Part of it was finding the right fit. But mostly, it just takes longer than anyone expects. Deals move slowly. Due diligence drags. Buyers get distracted. Financing falls through. Macro conditions change.

We also spent significant time exploring alternatives to a straight sale. Over the course of the process, we had serious merger conversations with 3-4 other footwear brands. The thesis was compelling: build a platform of like-minded brands with shared back-office operations while keeping the brands unique on the front-end. Each of these explorations took 3-6 months of work.

None of them worked out. The challenge with mergers is that everyone's incentives need to be perfectly aligned: the founders, the investors, the vision for what comes next. When you have multiple cap tables and multiple sets of stakeholders, getting everyone to the same place is incredibly difficult.

2. Most deals die

Of those 200+ conversations, maybe 20 turned into serious discussions. Of those, perhaps 5 got to the LOI stage. Of those, we closed with one.

Deals die for all kinds of reasons. The buyer's thesis changes. Financing conditions shift. Diligence surfaces something unexpected. The buyer gets distracted by another opportunity. Internal politics on their side. Valuation gaps that can't be bridged.

Learning to recognize when a deal isn't going to close saved me enormous time and emotional energy. Some signs:

• Slow responsiveness that keeps getting slower
• Requests for "just one more" piece of information, repeatedly
• Key decision-makers who are never available
• Vague timelines that keep slipping
• Excessive focus on problems without any discussion of solutions

When you see these patterns, it's often better to move on than to keep investing time in a dead deal.

3. Buyers are looking for reasons to say no

You've spent years building your business. You know every strength, every win, every reason it's valuable. Buyers come in looking for the opposite. Their job is to find risk.

Every number will be questioned. Every assumption challenged. Every weak spot probed. This isn't personal. It's how sophisticated buyers protect themselves.

The founders who do best in this environment are the ones who know what buyers will find before they find it. If you have customer concentration, acknowledge it upfront and explain your mitigation plan. If your margins compressed last year, have a clear narrative for why and what you're doing about it.

Surprises in diligence kill deals. The things you're hoping they won't notice? They'll notice. Better to surface them yourself and control the narrative.

4. Relationships matter more than process

I had conversations with buyers who ran formal, buttoned-up processes. I also had conversations that started casually and turned into real opportunities over time. The deal that eventually closed came from a relationship we'd been building for over a year.

Consumer brand M&A is a relationship business. The best buyers in the space know most of the brands they might want to acquire. They're tracking them, meeting founders at conferences, having coffee, staying in touch.

If you're not building those relationships now, you're limiting your options when it comes time to sell. The buyers who already know you, trust you, and understand your business will move faster and bid with more confidence than someone seeing your deck for the first time.

5. Your financials need to tell a story

Buyers don't just look at your numbers. They look at the trajectory, the consistency, the relationship between metrics. They're trying to understand how your business works and whether it will continue to work after they buy it.

The story your financials tell matters. Random swings in metrics raise questions. Inconsistencies between what you say and what the numbers show create doubt. Clear trends with logical explanations build confidence.

Before going to market, I'd recommend:

• Get your books clean. Seriously clean. No more "we'll fix that later."
• Understand your unit economics cold. By channel, by product, by customer cohort.
• Have clear explanations for any anomalies or trend breaks.
• Build a financial model that shows how value will grow for the buyer.

6. The turnaround helped

By 2023, Koio was losing money. COVID had hit. Privacy laws changed and online marketing got more expensive. Consumer spending dipped. The DTC playbook that worked in 2019 stopped working.

We spent the next 18 months in survival mode. We cut marketing costs, closed unprofitable stores and our offices. We let go of people we deeply cared about. We discontinued products we loved. We renegotiated every vendor contract. We turned a money-losing business profitable in 18 months. It was the hardest thing I'd ever done.

That turnaround story became an asset in the sale process. It showed that the business was resilient, that management could make hard decisions, and that the fundamentals were sound even if the growth story had changed.

Buyers liked seeing that we'd been through the fire and come out the other side. It gave them confidence that there wasn't more pain hiding beneath the surface.

7. You need to keep running the business

The worst thing you can do during a sale process is let the business slip. Buyers are watching. If results decline while you're in discussions, it raises questions. Are you distracted? Is the business weakening? Will this continue after close?

Keeping the business performing while managing a sale process is exhausting. It's like having two full-time jobs. But it's non-negotiable. The deals that close are the ones where the business keeps executing throughout the process.

8. Not all buyers are the same

I talked to strategics who wanted our brand and customer base. Private equity firms who wanted to roll us into a platform. Family offices looking for cash flow. Search fund operators who wanted to run it themselves.

Each type of buyer values different things, moves at different speeds, and has different deal structures. Understanding what each buyer actually wants helps you pitch more effectively and recognize which conversations are worth pursuing.

Some buyers will move fast and pay a premium for the right asset. Others will drag forever and nickel-and-dime you on terms. Learning to tell the difference early saves a lot of wasted effort.

What I'd tell a founder starting this process

Start earlier than you think you need to. Build relationships with potential buyers before you're ready to sell. Get your financials clean and your story clear. Know your weaknesses better than any buyer will, and have answers ready.

Prepare for it to take 3-4x longer than you expect. Prepare for most conversations to go nowhere. Prepare to be exhausted.

But also know that the right deal does exist. Finding it just takes persistence, preparation, and a willingness to keep going when deals fall apart.

Johannes and I started Koio as a passion project during our MBA. We bought a one-way ticket to Italy, knocked on 40+ factory doors, got rejected by most, until we found a family business willing to take a bet on two first-timers with no experience but a lot of passion. Our Brooklyn apartment doubled as our warehouse, showroom, and office. We personally shipped sneakers and celebrated the smallest wins.

Nearly ten years later, we found a partner who saw what we had built and wanted to take it further. The exit wasn't the highest offer we ever received. But it was the right fit: a buyer who understood the brand and could actually close. After three years of near-misses, that mattered more than squeezing out another turn of multiple.

If you're thinking about an exit, I'm happy to talk. Sometimes it helps to hear from someone who's been through it.