11 Questions Every Search Fund Investor Asked Me

It’s been a couple weeks. My family welcomed our second baby into the world, Hallie. Mom is doing great and Hallie’s diaper generator and vocal cords are more than fully functional. My son, aka no longer the center of the universe, also has proven new ranges in his vocal cords as he comes to understand these new truths. All is right in the world.

Onward.

If you're thinking about raising a search fund, one of the best things you can do is hear from someone who just did it. On May 1st when I was let go from my job, I immediately hit the phones and gave myself a 30 day crash course in everything they care about. Below is a breakdown of the 11 questions I was asked, why I believe they asked, and how I thought about answering.

This question is about showing that you didn’t just discover ETA last week and decide to raise a fund.

Only partly joking. Search is getting very popular outside of the Standford/Harvard crowd.

They’re trying to figure out how long you’ve been learning about the space, who you've talked to, and whether this is a serious effort.

I think a related question I often got was, "Who have you been talking to about search?" Investors want to hear names they recognize. I made sure to reference known searchers and other people in the ecosystem to show that I had done my homework, built relationships, and wasn’t going to change my mind about this path next month.

Have a draft of a future issue on why search fund investors are kind of a cartel. Who you are is a really big deal so name drop as much as you can.

Like any interview, they want to get to know you.

They’re listening for pivotal experiences that shaped how you operate. What do you think is worth mentioning your story.

In my case, they always asked about my time in the Navy. I was asked a lot of follow-up questions about what I did there, how I handled leadership challenges, and what I took away from those experiences.

This is where it helps to have told your story many times before. You want it to be consistent across conversations. Investors share notes. You’re likely to talk to more than one person at a firm, and they’ll catch inconsistencies. So you want to have your story tight, practiced, and ready.

This usually comes up in your backstory, not as a separate question. But they’re always listening for it.

Investors are looking for moments where you stepped up and took real ownership. They’re backing you to be the CEO of a company with 10 to 100 employees. If they don’t believe you can lead people, they’ll see that as a major risk.

One story I always highlighted was from my time at GWorks.

A VP suddenly quit on a Friday afternoon, and I was asked to step in and keep the trains moving. It was a stressful time. We had recently lost other software engineers, and I focused heavily on retention.

I prioritized people. I had one-on-ones, made sure everyone felt heard, and did what I could to stabilize the team. At the same time, I tried to maintain sprint deliverables and keep momentum. It taught me to lead during uncertainty by focusing on the team first.

They ate this up because this is a real thing that can happen in small business. Having stories like this lined up that you can casually drop in conversation will get them excited to hear what you did and further qualify you.

This question comes up after they’ve seen your thesis. If you’re on a first call, that means they already saw your PPM or a summary of your target industry and didn’t have a major issue with it. If they did have a problem with the space, they wouldn’t take the meeting.

They’re not asking you to justify the market so much as they’re looking for signals that you understand how it works.

They want to hear you speak fluently about how the space is structured, what kinds of businesses exist within it, and where the opportunity lies. Specificity matters.

Expect to be asked about market size, types of sub markets within, how many companies meet your criteria, and other specifics. You need to have done your home work here and it certainly helps if you have had time in an industry already.

This gets asked when you’re pursuing a space you’ve already worked in. Investors want to know why you are the person to go after this, especially if they have other searchers looking at the same space.

They want to know how your insights are going to help you outperform others.

I framed this around lessons I learned from firsthand experience. In some cases, I had views that were different from investors’ assumptions. THIS ISN’T NECESSARILY A BAD THING.

Most search investors are generalists so their thought processes will be more general unless they’ve worked or backed someone in space already.

If you have a particular point of view, this is the time to share it and double down on it. I had several investors previously not showing a lot of interest really perk up when I said things that were counter narrative because you couldn’t have had that viewpoint without time in industry.

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This question came up in nearly every conversation.

At first, I didn’t know why it was such a big deal, so I started asking investors why they cared so much. The answers I got were all over the place, but the main thing I think they wanted to see was that I had thought about it.

My answer was that I wanted a mix of institutional investors and operators.

Institutional capital brings deal reps and transaction experience.

Operator capital brings help post-close when real business problems show up.

I told them I wasn’t just looking to raise money from anyone with a checkbook. I wanted people who could support the journey from multiple angles.

If you’re doing a solo search, you’ll get this question. I got it from almost every investor.

I think I also got it so often because I didn’t fit the typical profile.

I didn’t go to a top MBA program. I

didn’t have private equity experience.

And so I think some investors were looking for added validation. They might have been more comfortable backing me if I had a partner who checked those boxes.

My answer was that I wasn’t against it, but I hadn’t met the right person. I think a search partnership is a big commitment. You need deep trust, shared values, and the ability to problem-solve together. I hadn’t found that yet. That was usually well received.

One thing that came up in follow-ups was, who do you lean on? Who’s in your corner? That’s really what they’re getting at. If you’re a solo searcher, you need to show you have a support network, even if it’s not a partner.

If you’re going down this path you probably have people already, but if you don’t, you need to get there. I’ve been leading a peer group of veteran business owners for a few years which has been an invaluable resource. I was also able to talk about the network I’d developed through the podcast.

This is the inverse of the "why this industry" question. Investors will often challenge you based on what they think they know.

In my case, GovTech was known for long sales cycles and bureaucracy. And some investors had negative experiences selling into government or had heard horror stories.

At a certain point, I started naming those risks before they could. I’d say, "You might be wondering about long sales cycles" and then walk through why I didn’t think that was a blocker. That was a powerful move. It made me look prepared, confident, and credible.

And here’s the thing: sometimes they were right.

Some of the concerns they raised were real. But I had seen ways to work around them. I tried to meet them where they were, show respect for the concern, and then offer a counterpoint from experience.

I even had one investor say no because we just didn’t agree on the market. I told them, respectfully, that I thought their take was short-sighted based on what I had seen. It didn’t change their mind, but that’s okay. Not everyone is going to see it the same way.

Raising money is about more than getting a check. It’s a partnership. They want to see how you think and conversely you should be interviewing them just as much to see if they’ll be a good partner to you (beyond money).

You don’t have to agree on market dynamics to have a good relationship. It is helpful to agree on problem solving and how to address certain business issues.

I’m not sure if this is common or a good idea, but anyone that disagreed with me I called them on it. Asked them why they thought that way. Asked what evidence they had to support their claims.

Don’t shy away from making a two way conversation.

This was one of the most common questions. It’s trying to uncover whether you actually understand what running a search looks like. Investors are trying to weed out people who think this is just cold emailing from your laptop and waiting for a deal to fall in your lap.

I talked about treating it like a sales process. You need a target list, a cadence, a follow-up strategy, and the willingness to get on a plane.

They want to know that you’re going to meet people in person. They want to hear that you’re willing to do the uncomfortable stuff.

I used my podcast as an example of outbound relationship-building. I’ve had over 100 guests. That’s all cold outreach, prep, follow-up, and long-form conversations. I also referenced my M&A experience from my last role, where I helped close two acquisitions. That was less impactful than I expected, but it still helped.

This is closely tied to the sourcing question. The space is getting more crowded. Investors want to hear how you’ll compete.

My take? There isn’t a lot of real innovation in how people run searches. Everyone talks about follow-up, CRMs, and personalization.

That’s all table stakes.

I focused on showing that I’ve actually done the basics really well, consistently. This seemed to be well received.

Again, I leaned on the podcast. That shows I can build rapport and follow through. I also mentioned my previous M&A work and how I built relationships with sellers. Most people say they’ll fly out to meet owners but many don’t.

Differentiation isn’t about being flashy. It’s about doing the hard stuff and not quitting.

This came up every time. In early conversations, and especially in follow-ups. They’re trying to gauge momentum and social proof. Are other smart investors backing you? If not, why not?

I learned quickly to always have an update. If someone asked, I wanted to be able to say, "We’re 60% raised" or "Two more people joined since we last spoke."

That created urgency.

And when someone passed, I followed up hard for feedback.

Sometimes they didn’t share their concerns during the call, but they would in writing later. That helped me improve how I pitched.

Many will give the blanket “We’re just so swamped right now” or “There’s a lot of great candidates out there” stuff, but a few, if you’re likable and genuine, will give you honest feedback if you’re sincere in your ask and show a desire to improve.

If you’re a prospective searcher, I hope this gives you something to work with. These are the real conversations, and if you can prepare thoughtful answers to these questions, you’ll be ahead of most.

Have another update coming next week on where I’m at with my raise (good news!). If you’re raising or thinking about raising and want to chat, would be happy to share my experience and offer any insight I can to help see you succeed. This community is small and I know for a fact that nobody does it solo.

Have a happy 4th. MERICA!

PS.

I’ve been vibe coding my little heart out the last few weeks. Have built a few cool projects, but this is one I’m most proud of.

It’s called Saved Send.

It pulls all your bookmarks from X, lets you organize them, and then emails you one per day so you can get rid of what I call ‘bookmark debt’ (you see something, bookmark it to read later, then never come back to it).

I’m running a lifetime pricing deal to get off the ground which I lose a lot of money on because the X Api is expensive.

Your gain.

Check it out - Saved Send