Key Takeaways
- Independent investment bankers close more deals by prioritizing relationships over transactions. Shawn Flynn's framework centers on knowing both the client and the buyer as people — their mental state, their goals, and their communication style — before a single LOI is signed.
- Consistent, proactive communication is the single biggest factor in preventing deals from dying. "Time kills all deals" because silence breeds doubt. Regular check-ins with both sides keep momentum alive and surface problems early enough to solve them.
- Coachable clients close faster. The most important pre-engagement signal isn't a company's financials — it's whether the founder sees the banker as a trusted Sherpa or just a service provider.
- A podcast is one of the most effective business development tools available to independent bankers. It creates relationship entry points with high-caliber prospects who would never respond to a cold email, and it builds credibility at scale before a deal is ever discussed.
- Going independent is less risky than it feels. The biggest fear — that clients won't follow you — almost never materializes if the relationships were real to begin with.
- AI is already reshaping how independent M&A advisors work, from CIM creation to buyer list expansion to deal preparation. Smaller, nimble shops have a structural advantage over large firms that are slow to adopt new workflows.
- Every deal dies at least two or three times. The advisors who close are the ones with relationships strong enough to have honest conversations when things go wrong.
Full Transcript
Shawn Flynn: And then he turns, he just looks at me and goes, "If I had known, I wouldn't have talked to you." And I was like, what? And then a moment later he goes, "But I might have a deal for you."
Abby Roberts: Shawn, thank you so much for coming on our new Closers Podcast, where we explore the secrets of successful independent deal makers like yourself with Finalis. I wanted to kick off by saying I found a lot of things in your background that were very interesting. I won't get too deep into the MMA fighter documentary, although I'm very curious about that. And I want to ask about the Silicon Valley podcast, because you run your own podcast as well, which is super interesting — bankers are not necessarily known for running podcasts, although maybe that's the new thing. But let's start with the MMA fighter documentary. How did that happen?
Shawn Flynn: So, I was living in Beijing, China. I lived there for about five years. When I was there, I wanted to do everything with the local Chinese, so I went to a local Chinese gym. I ended up at a jujitsu gym called China Top Team — it had the best Chinese fighters training for MMA. John Chieh-Chuen, Li Zhenlan. But this was before any of them had found the UFC.
I'm training with these guys and their stories are incredible. Some had never gone to high school, some couldn't read — and this is China, where the literate population is pretty much everyone. They were all living in one room in a hotel across from the gym, eight people to a room. And you're thinking: why are these people doing this? They're always hurt, always injured, and they keep going. They see it as their opportunity.
So I thought, I want to record this. I want to make a documentary. I followed them, interviewed them, asked them a bunch of questions. I even pitched it to a producer in Ireland. It never went anywhere — I didn't know anything about producing documentaries; I just captured the content and tried to pitch it. But it was incredible just to hear the stories of these people, most of them from inner Mongolia, growing up wrestling and doing everything, thinking one day there could be this huge opportunity to fight at the UFC. Some of them, since then — and this was about 13 years ago — some of them have made it. I still have the footage. Maybe now it's valuable. If anyone ever makes a documentary on Chinese UFC fighters, please ping me.
Abby Roberts: Looking at your background, I can see that you have this very broad-based curiosity about the world. I wonder if that's how the Silicon Valley podcast got its start.
Shawn Flynn: I wish that was it. Honestly, it was more laziness. For a number of years I was helping companies in Silicon Valley set up in tech parks in China, and Chinese companies set up in Silicon Valley. Very similar conversations over and over — here's a lawyer for your IP, here's an HR company, here's commercial real estate. I was doing a group called Leadership MountainView, where you'd get together monthly and learn about the city. Representatives from Google, LinkedIn, Adobe would attend.
One day they said we're going to visit the public access station. I was thinking Wayne's World. And I thought — I can record all these service providers, create this reference library, and whenever I bring over a company I can just say, "Look at episodes four, eight, and twelve." The interviews would cover 90% of that first meeting.
I ended up doing 46 interviews, and it ended up on 28 public access stations across the US — one of them was LA 36, which has a couple million viewers. From that, I got connected with The Investors Podcast Network, a top financial podcast with something like 200 million downloads at this point. They wanted to do a podcast about Silicon Valley, and we did a short run together. Then the pandemic happened and I wanted to keep going, so I rebranded and launched the Silicon Valley Podcast.
Since then I've interviewed founders from Square, Intel Capital, Juniper Networks. I have an episode going live shortly where I interviewed the person who introduced Steve Wozniak to Steve Jobs — the interview was for Apple's 50th anniversary at the Computer History Museum. I've just been able to sit down with incredible people. Why? Because everyone wants to talk to a podcast host. No one wants to talk to an investment banker. It's a great foot in the door, a great way to meet high-caliber people with no one's guard up. It's casual, it's a conversation, and it's a great way to build a relationship.
Abby Roberts: You create that space where you're not pitching anything — you're just learning and keeping things open.
Shawn Flynn: It's totally a safe zone. You're cracking jokes, talking about everything other than a deal. And it can be kind of funny. There's one person I interviewed for the podcast — he'd taken a company public in Japan and was working on a company here that was probably the first use of blockchain to solve a real-world problem.
After the interview, he invites me over for dinner. A week later I'm at his place and he goes, "How do you make a living as a podcast host?" I told him I don't make money from the podcast — it's just my passion project, a reference library for anyone in the world to access Silicon Valley. He goes, "Wait, what do you do then?" I said, "Oh, I'm an investment banker."
And there was a pause.
And then he turns and looks at me and goes, "If I had known, I wouldn't have talked to you." And then a moment later: "But I might have a deal for you."
That is so true. People have a stigma. But if you build a relationship first, it's different.
Abby Roberts: I have to laugh — back in my journalism days, people would have the same reaction when I said I was a journalist. They'd literally run away from me.
Shawn Flynn: And how'd you get them then? Were you like, "Oh, I have a Pinterest page, let's talk"?
Abby Roberts: It was really about catching them at the right moment — usually right after someone had closed a deal and they were high on life and willing to talk. And then you'd build up that trust. But yeah, a lot of them were panicked, especially if I was chasing them down streets or in elevators — which has been known to happen.
Shawn Flynn: Turn the corner just at the right moment, accidentally bump into each other.
Abby Roberts: Exactly. Or I'd sit in the front row of conferences and look at someone intently so they'd be primed to talk to me right afterwards.
Abby Roberts: But given all that — how did you end up in investment banking? You didn't go the traditional path.
Shawn Flynn: Yeah. One of the most common things PE people say to me is, "We looked you up — you majored in mechanical engineering with a minor in theater. How does that work?"
I didn't go to an Ivy League school or get an MBA. From college, I went overseas, started a couple of companies, got operating experience. When I came back to the US after exiting my last company, I got involved with an angel group in Silicon Valley — I went from volunteer to investment director at the second-oldest angel group in the area, which was incredible. You're in a room with angel investors who had taken companies public, had major exits, just incredible careers. And their job, apparently, was to challenge everything the investment director said.
One of my favorite stories: I did a two-page write-up on a wearable company and presented it to the group. The next day, one of the gentlemen comes up to me and says, "Shawn, that report you did — we talked about it all last night at the bar. We've never laughed so hard in our lives." I just took it as incredible feedback. Every time I met that group it was like an MBA course. I was just learning from people who had had such successful careers.
In that process, I started doing cross-border partnerships. We had Silicon Valley relationships going back 20 or 30 years, and there was new money coming in from China. I had lived in China, spoke Chinese. So let's connect the dots. That led to working for a Chinese company, helping Silicon Valley companies set up in China and vice versa — but in the process, you're packaging companies, helping them with their presentations, getting them ready for investors. It was essentially investment banking. Except I was just making introductions and not getting paid for it.
I remember one bank telling me, "Shawn, thanks for the intro — we made a ton of money." And I thought, wait, that's not how this is supposed to work. Eventually one bank said, "We don't want you to make intros to anyone else anymore. We'll sponsor all your licenses, come on board." That was my first investment bank. After a few years, then another bank, and then after six-plus years total, I branched off into SVH Capital. It was a natural progression, looking back.
Abby Roberts: You had all that real-world operating experience before ever going to a bank. What was your perception of how investment banks typically approach deals?
Shawn Flynn: Honestly, I just don't think most bankers understand the life of a founder or an operator. They look at the numbers — margins, projections — but they don't think to ask: how are you doing? How's your mental state? Are you still emotionally engaged in this company? How's your team?
Until you've had to empty your bank account to make payroll because a client didn't pay, I don't think you can really relate to these founders. I had that experience in China. I had money saved, was planning a trip to Tibet, had this one big account — and then something happened with the team and the client decided not to pay. I had to use everything I'd saved to cover payroll. Still haven't been to Tibet. But as a founder, it's your responsibility to make sure your staff gets paid.
I don't think many of my peers have experienced anything like that. Most of them also grew up in relatively comfortable environments, went to great schools, their "international experience" was a semester abroad. Whereas Silicon Valley is full of founders from all over the world, with wildly different life stories. I'll have conversations with bankers and they'll say, "That reminds me of my semester abroad in Spain." And I'm like... okay. Let's see where this goes.
I think that's actually what sets me apart, and my team at SVH Capital. We have people with genuinely diverse international backgrounds — Bennett from Ghana, Holly, Jason — and bringing those perspectives to deals is powerful.
Abby Roberts: The international angle is super interesting. I've seen so many US people almost sneer at cross-border deals, and the poor people in EMEA and APAC are always saying, "Every market is different," and having to explain it over and over to Americans who still don't quite believe them.
Shawn Flynn: Working and living in another country — there's nothing else where you can learn as much in such a short amount of time. Anyone listening: take the opportunity. Live abroad for a while, work abroad, try to be like a local. You'll learn more in that time than almost anything else you can do.
Abby Roberts: So when you decided to go out on your own, what was that like? What were you weighing, what were you thinking about?
Shawn Flynn: I had known Fed for years before switching over to Finalis. I saw what was being built and thought, okay, this is the right time. There's a real opportunity here.
But when you go out on your own, there's so much doubt at the beginning. I was panicking — no one's going to work with a one-person shop. And it was hilarious, because when I finally did branch off, I started telling everyone. And their reaction was: "Wait, what? I thought your previous firm was your place." Multiple people said that. They just assumed it was mine based on how I'd talked about everything. That gave me real confidence — okay, maybe I've already been running this in people's minds.
And then the other big fear: would the people I'd built relationships with follow me, or would they stay with the old firm? Every single person said, "Shawn, we built a relationship with you. If you go, we follow." That was the biggest hurdle. Trust me, I was having cold sweats at night — I'm going to be broke for years, I want to start a family, all of that. But after a couple of months of conversations, that fear was gone.
Then it was all the small stuff. Getting a name — that was almost two weeks. I was on GoDaddy, looking at what was available, then I realized I could just type what I wanted into ChatGPT and ask for available domains. Except at that point I didn't really know how to write prompts, so it kept suggesting great names that turned out to cost $50,000. And then I found out you can't have "bank" in your name in California unless you're actually a FDIC-insured bank. There went a lot of the domains I'd found.
Then branding, the website — this is years ago, so it was WordPress, drag this, drop that, another week gone. And then the email footer. I thought that was going to take ten minutes. It took five hours because of the photo sizing. My wife ended up doing it for me.
Abby Roberts: I went through a very similar journey about a year ago — decision paralysis on GoDaddy, all of it.
Shawn Flynn: It's all those little things you don't even think about. Business cards, email provider, do you go Google or Microsoft. Every decision feels like it impacts everything forever. And you just want to do deals. But hopefully in the future there'll be a ready-made checklist: here are the 50 action items to go from zero to operational investment bank on the Finalis platform.
Abby Roberts: And speaking of deals — the theme of this podcast is really about closing. The deal life cycle, I always picture it like the salmon journey. Most of them die along the way. Only a few make it to the end. What was your first deal close like?
Shawn Flynn: My first real deal — start to finish, just me — was selling a company to DuckDuckGo. It was DuckDuckGo's first acquisition. I represented the founders of Removely; it's been written up in TechCrunch, so it's public. It was incredible because everyone involved was good people — no combativeness, everyone wanted the deal to happen, great atmosphere throughout.
And it was 100% virtual. This was during the pandemic. I wasn't even sure a deal could be done without meeting in person — I was worried about how you build a relationship, how do you get a client to sign an engagement without meeting face to face. But it happened. The clients were happy, DuckDuckGo was happy. I did everything. And my celebration was... sitting in front of my computer watching a movie. No restaurants, couldn't meet anyone. But I sat there thinking, I did this. That was me.
Abby Roberts: What do you think the secret is to closing deals? Where do deals often go wrong, and how do you avoid those pitfalls?
Shawn Flynn: A lot of it comes down to the relationship that's established early on — specifically, does the client feel comfortable asking you questions, and do you feel comfortable telling them what they need to hear, not just what they want to hear?
If you have that relationship at the very beginning, you can set realistic expectations before going to market — on timing, on valuation, all of it. You also get to understand your client's mental state and track it throughout the journey. You can see when something's off. Is it the transaction, or did something happen with the business? And you stay in consistent communication throughout — not just a bi-weekly status report or a Friday fifteen-minute call, but quick check-ins, a few emails, "how are you doing?"
That goes for both sides of the table, by the way. Once you're in confirmatory due diligence with a potential buyer, that relationship matters too. When things go silent, people start doubting. Shiny new options appear. Time kills all deals — and that's true because silence gives doubt room to grow.
But if you're in constant communication, you know what both sides are thinking. You've asked the buyer: of your last ten deals, how many closed after the LOI? Did you do any retrads? You've had dinner with them. You've built the kind of relationship where you can say, "I know they want to get this done and they're a good fit for your client." You're able to assess in real time instead of just guessing.
When someone tells me a deal died and I ask them what happened, and they keep saying "I don't know, I don't know" — I'm thinking: you didn't notice the person went on a trip for two weeks and didn't contact you? You didn't see that as a warning sign?
Abby Roberts: The emotional component of deal-making is so critical. But you also mentioned something important earlier — not just celebrating when someone wants to do a deal, but being selective: doing due diligence on your clients, picking good buyers, being comfortable saying no. How do you evaluate whether a client is the right fit?
Shawn Flynn: One of the biggest things is: do they have realistic expectations? You'll talk to people who say, "I'm not selling for anything less than this number," and you think, well, I guess you're never selling. Some bankers will sign that engagement anyway, thinking the market will adjust the client's expectations. That's not always true.
So first: is this client coachable? Do they see you as an expert in transactions, or do they think they're the smartest person in the room because they founded and scaled this company? That second client is very challenging. You want the one who says, "I know what I don't know. I want a Sherpa. I want a guide to get me to the top safely."
And timing — you want a client who understands it might take a year or two to get ready for the exit they actually want, not one who says "it's November, I want to close by December." You also want a client who says they'll get you documents by Thursday and actually does it.
There are signs even before signing an engagement. This person is going to be a great client, or this is going to be painful. One of my own tests: am I happy when they call me out of nowhere? Or do I see their number pop up and think, "Oh no, this is going to be a rough half-hour"? That feeling matters.
On the buyer side, it's similar. Who's the right fit for this client, not just on paper but in terms of personality and goals? You might have four LOIs in front of you, and three of them have better numbers, but the conversations you've had with the fourth tell you they're the right fit. That advice — "look more closely at this one" — is super valuable.
Abby Roberts: It must require real self-discipline, because that pot of money at the end of a deal is always tempting, even when the client isn't right.
Shawn Flynn: Hopefully you have a big enough pipeline that you get to be selective. You only have so many hours in the day. If you're filling your bandwidth with the wrong deals, you can't work on the right ones. And if you have a podcast out there where potential clients are seeing you and thinking, "This person clearly has deep roots in Silicon Valley and a real network" — and they reach out — then good times.
Abby Roberts: I have to laugh because marketing is clearly something you're very good at. As head of marketing at Finalis, I'm always trying to get bankers to let us amplify their deals and build their presence — and not everyone is enthusiastic about it, which shocks me.
Shawn Flynn: A lot of investment bankers almost treat marketing as beneath them — especially the ones with the top MBA credentials. "I'm above social media." Which sounds a lot like saying you're above doing deals and making money. I think part of it is fear. They're used to having a biz dev team, a sales team, deals coming to them. Building your own pipeline, putting yourself out there publicly, building trust with potential clients you've never met — that's genuinely hard. It's something a lot of bankers have to get over if they want to succeed independently.
But it's fun. Being on podcasts is fun. Being on stage is fun. Moderating panels is fun. At first I was scared — I was terrified. Want to hear a funny story? My very first podcast interview was with Melanie Perkins, founder of Canva. I know. First interview.
The problem was we had prepared a question set for 45 minutes, but Melanie's answers were so tight and precise that we burned through everything in about 22 minutes. I had to tell her: "This has been fantastic, but I really need 45 minutes of content and we've run out of questions." So the three of us — me, Melanie, and her CMO — are on a Zoom brainstorming new questions together. And I'm sitting there sweating, thinking I'm so unprepared, this is so unprofessional. And she's just like, "Sure, let's brainstorm. We'll make it work." Just the most casual, generous conversation.
It was probably around episode 15 before I really felt comfortable just having conversations with people. That's when it clicked — these are just people.
Abby Roberts: Do you have a favorite question that gets them off their rehearsed talk track?
Shawn Flynn: Before any interview I do a 30-minute prep session. And the one question I always ask is: "You've been interviewed by so many people over the years. What's one question or topic that you've always wanted someone to ask you but never have?"
And they sit there and go, "Oh, that's a good one. Huh." And then they start brainstorming. "We could talk about this, and then maybe this." I take notes. By the time the interview happens, they're ready to go and we're covering things I never would have thought to ask — things they've actually wanted to share. People love stories, they love action items. That's the best content. And then one thing feeds into another, and next thing you know 45 minutes to an hour has gone by.
Abby Roberts: So Shawn — what have you always wanted to talk about and never had the opportunity?
Shawn Flynn: What's next for SVH Capital. That's the big thing on my mind lately.
I look at AI right now as an incredible tool. But I also think about the future — when does it get to the point where a potential client just uses AI to do all the matchmaking and analysis? Where it's essentially AI talking to AI, working out the terms, and there's almost no human in the loop?
How far away are we from that? Should I be building out a team and training people? Or thinking more about building AI agent workflows? Probably some combination of both. But I think this is actually a huge opportunity for small shops — because many of the larger, more established firms aren't nimble. They're set in their ways. "We've done deals this way for 30 years." Great. Thank you. Your clients are going to hear about the Closers Podcast, and while you're sitting there too attached to your old playbook to promote yourself, we're out here building relationships at scale.
The next five years are going to be fascinating.
Abby Roberts: It's such a tough existential question we all have to sit with. I was talking to someone the other day and thought, what are my kids going to do? Is college even the same proposition anymore? And then I go outside the world of people obsessed with AI and everyone's like, "Why are you having daily panic attacks about this?" And I'm like — no, it's real, it's happening.
Shawn Flynn: I was at an ACG event recently — the annual five tech trends — and one of the five speakers on the panel was literally a robot. An AI robot, waste up, in a chair. Someone asked it when we'll see robots in every home. Its answer: in Silicon Valley, three to five years. The rest of the US, thirty years. Which was weirdly insightful. Here we have Waymo and driverless cars and it's been happening for years — but you go anywhere else and it's the Jetsons.
Abby Roberts: What do you use AI for practically, day to day, in your deal work?
Shawn Flynn: Everything. Creating the CIM — I type in a description and get a design direction that's 90% of the way there, then I just send it to the designer with a small tweak. Wording and drafting. Finding information inside a data room. And one of my favorite uses: I upload material into NotebookLM and create a custom podcast on whatever I'm working on — and I'll listen to it on a walk before a client call, bringing me up to speed on the market, the sector, the competition. At 1.5x or 2x speed. It's incredible for reviewing things in a way that's actually engaging.
You can also use it to build teasers and quizzes on deals — quiz yourself, quiz your team. Imagine associates getting quizzed by the MD at 2am on a Saturday. "Here are five questions on the deal. Answer them."
And then buyer lists — I love asking AI, "Here are the obvious candidates. What questions should I be asking myself to expand this list?" It gives me ten questions. I feed those back through. Next thing you know, I've found 20% more potential buyers than the research team had. The use cases just keep going.
Abby Roberts: How do you make sure people actually digest all of this, though? When you can spin up a research report in two minutes, how do you make sure people are really reading and thinking through it?
Shawn Flynn: Yeah. I mean, a lot of people weren't really thinking things through to begin with. But maybe that becomes the real differentiator going forward — does this person actually understand, or did they just read the five bullet points? Did they actually read? Time will tell.
Abby Roberts: And on that note, we've covered so much ground. But if I were to summarize what you're saying on the deal side: you close deals because you know your client and you know the buyer. It really comes down to the relationship.
Shawn Flynn: If people are talking, deals get accomplished. That's the thing newcomers to this industry often underestimate. When communication stops or emotions go in a negative direction, things get derailed. And that ties back to "time kills all deals" — why did time kill it? New information? Someone got distracted? Something was left unsaid?
But if there are open lines of communication, even when deals get derailed — and they always do, everything dies two or three times — you're able to bring them back. You can find out what's really going on and get things past the finish line.
Abby Roberts: Tell me one more story — a time a deal was dying, something was off, and you managed to get it back on track.
Shawn Flynn: That's every deal. Every deal dies multiple times.
A lot of it is just sitting down with your client and asking, "What's really going on?" Sometimes you hear about something with the family, or a stress they haven't told you about, or a key client that didn't renew. Or hypothetically — there might be a situation where engineers who are overseas go missing during a geopolitical crisis and everyone is frozen, because they need those people to sign certain documents. And the deal goes on pause for months while everyone is just praying for those people to be found safe. And a few months later, they are, and the deal can continue.
In situations like that, you have to be able to say: okay, let's take this day by day. Let's calm down. What are the options? Best case, worst case? How do we communicate this to the potential buyer in a way they'll understand? Deals can die for countless reasons — and be revived for countless reasons. But only if the relationships are strong enough to have those conversations.
Abby Roberts: And patient enough to survive wild hypotheticals like that one.
Shawn Flynn: There are so many in this industry. Most of them never see the light of day.
Abby Roberts: It's been really great learning more about you and how you approach deals.
Shawn Flynn: It's been a pleasure and an honor to be on this podcast. And Abby, I'm always open — please consider welcoming me back for a future episode. Hopefully your audience got a couple of tidbits from this conversation.
The content provided is for general informational purposes only and should not be considered a recommendation or personal advice. Finalis Securities LLC is a broker-dealer registered with FINRA and a SIPC member firm. Check out the background of this firm on Brokercheck.© Finalis Securities LLC, 450 Lexington Ave, 4th Fl, New York, NY 10163, United States