Key Takeaways
- Coming from entrepreneurship is an underrated path into investment banking. Dale built his practice on 12+ years of operating experience, which gave him pattern recognition, resourcefulness, and genuine empathy for the founders and sponsors he advises.
- Deliberate focus is a competitive advantage. By choosing a Series 82 license and limiting his practice strictly to private placements, Dale removed the temptation to chase every deal type and instead built deep expertise and a referral-driven pipeline.
- A "can you, should you" filter applies to almost every decision. Whether evaluating a deal opportunity or a life choice, this two-question framework separates the critical from the non-critical and prevents wasted effort.
- At least ten variables must align for a capital raise to close. Investor timing, sector fit, check size, company stage, deal structure, geography, existing portfolio conflicts, syndication capacity, funder criteria, and more all have to line up simultaneously — the banker's job is to nudge each one in the right direction.
- Compliance isn't just a regulatory requirement — it's a due diligence tool. Dale uses the FINRA registration process and Finalis framework proactively to vet deals and sponsors, letting the checklist surface bad fits before he invests time and reputation.
- Trust is the currency of the business. Leading with "how can I help you" rather than "what can you do for me" has meant Dale hasn't had to actively prospect for deals in over three years — referrals have covered it.
- AI is the mentor Dale never had. Without a Wall Street background, he uses Perplexity and other AI tools to rapidly develop industry context, draft materials, and identify funders — getting 90% of the way there before the first cup of coffee.
Full Transcript
Amy Pisano: Well, hello, welcome to the Closers Podcast. Today we are very excited to have Dale Sizemore joining us. Dale, thank you for joining.
Dale Sizemore: My pleasure, Amy. It's good to be able to share ideas together.
Amy Pisano: Thank you so much. Well, why don't we get started with a bit of background. I know you've had a very diverse start and have worked in a lot of different areas. Tell us how you got into banking and M&A advisory.
Dale Sizemore: Thank you. This has been an interesting journey. I came to investment banking through the entrepreneurial journey. I would be considered a serial entrepreneur — I had two companies that I started and ran, and each of them lasted over five years. Through that, a lot of the topics that come up between entrepreneurs are funding and how that all works. Then I had the opportunity of moving beyond that into actually being on the funding side.
So I got myself licensed and decided to get into my Series 82, which I very specifically chose for private placements. That's where my skills are, that's where the focus is, and it keeps me from being tempted to go into M&A, retail, IPOs, and things like that. I wanted to be a single banker — a very boutique, concierge level of handholding. This allows me to do that. I've been very pleased with the experiences I've had both with Finalis and in the banking industry.
Amy Pisano: I know that's something we spoke about last week — this idea of what you could and should do. It sounds like focus has been an essential part of your career.
Dale Sizemore: I'm reminded of it every day. I use the lens of "can you, should you" for most of my life decisions, whether that's a banking opportunity, a vacation, or where to go to eat. It's a very good filter for most people in most things in life. It allows you to think things through, and it removes the critical from the non-critical.
Amy Pisano: I love it. Another thing you talked about is that you consider yourself relentlessly resourceful. How did that lead you to build your own practice?
Dale Sizemore: A lot of it came from the entrepreneurial experience. When you're starting a company on your own and it's a small business, you end up having to do a lot of things with limited or no resources. You become very resourceful about what's available and what's a priority. That carried over into investment banking, because there are so many variables, so many different kinds of projects to learn. An opportunity comes by, you have to learn about it quickly — the business opportunity, the industry, the competition, who the funders might be. That quick-study ability comes from 12-plus years of entrepreneurial background.
Amy Pisano: Do you remember your first transaction?
Dale Sizemore: Yes, I do. With any transaction, whether it's the first or the last, the common denominator for me is that you've solved a problem for people who trusted themselves to you. That's what's meaningful. I haven't had to go look for a deal in the last three and a half years — clients refer me to someone else, and then someone else. What's heartwarming is that people are trusting their lives, their families, their businesses with an important decision. That really captures what the first deal was about.
Amy Pisano: As someone who's spent my career in sales, I'd love to hear your perspective on keeping a network warm. You said you haven't had to look for any deals — what's the magic?
Dale Sizemore: The magic is being respectful of other people. Don't lead with your hand out — lead with your heart out. Start with "how can I help you?" It may not be something I can do, but I may know somebody who can. It's rare that I just flat-out say no to someone. It's typically: that's not where I can add the best value, let me find out who I can refer you to. People do that for me all the time. Why not extend the same to others?
Amy Pisano: Another thing you talked about that really piqued my interest was how many things need to align for a deal to close. It sounds similar to "time kills all deals," but you have a more specific formula.
Dale Sizemore: Yeah, I just jotted these down one day wondering why this stuff takes so long and why it's so hard. I came up with nine of them, and today another one was added. Let me hit the highlights without being depressing.
The timing of the investor — whether debt or equity. Some won't talk and then pop up like whack-a-moles, suddenly ready to go. Is this the right sector for those investors? Do they even do it? The size of the funding amount — I've had investors say "don't bring me anything less than $150 million," and I've got one that says no to anything over $100 million. You have to align with their expectations.
The stage of the company matters. Some people are very receptive to early stage and others aren't. With AI and data centers, we've seen traditional funders shift — a fear of missing out has them looking at earlier-stage projects than they used to. Then it's debt or equity, or some combination.
Geography is another one. People say they're global, but are they really? I went to Saudi Arabia and they said they were global — in practice, they focus on the MENA region. That's fine, but it's not global. If you're investing in the Caribbean, is there currency risk? In Costa Rica, you don't really have fee simple property rights. In Belize, you do.
Then there's the question of whether the investor has already invested in that same sector — are they just extracting your brain for intel on their existing portfolio company? Is the investor going to syndicate? A hundred-million-dollar fund sounds like a lot until you realize they typically invest half, keep the rest for dry powder, and would never put $50 million into one company. All of a sudden that $100 million fund is $5 million for practical purposes.
And today there's additional criteria specific to sectors. On data centers, for example: do you have power? Do you have the land under contract? Do you have permits? Do you have an offtake agreement? If you don't have those answers, stop talking. All of those have to align. Our job as the banker is to nudge them in the right direction, steer expectations, and set everyone up for reality.
Amy Pisano: Right, and I would imagine helping them avoid surprises, because many of them haven't seen the movie quite as many times.
Dale Sizemore: Yeah, entrepreneurship and investment banking are a lot like being a parent. I'm not sure if we knew what we were getting into, we'd still do it. But we're in it now, so we just make the best of it.
Amy Pisano: So those are some tough odds. What keeps you going when a deal looks like it's going to stall?
Dale Sizemore: I try to stay optimistic, because when you think about it from a business perspective, there are a lot of people who have to do something. Investors have to put their money to use. People have good projects evolving all the time. It's just a matter of: how do we match them? How do we make it happen? It's going to happen. There are people out there doing it every day. The next one comes along. Today I got some wonderful news. If you'd asked me yesterday, I had a different choice of beverages.
Amy Pisano: Well, I'm glad we caught you today. What separates the advisors who are constantly closing deals from those who are hopelessly optimistic and chasing?
Dale Sizemore: Luck is always part of it — it's a missing ingredient in the recipe, but it's not the only ingredient. What separates the people who do well is how well they know the industry, how quickly they can assimilate information and apply it from both sides — the investor's perspective and the sponsor's perspective. Curiosity goes a long way. Looking over the horizon, thinking two or three steps ahead, having a plan B and C. Then polite perseverance. And a willingness to help people even when it doesn't work out — they'll remember it. If you tried to help them and it didn't come together this time, maybe next time it will.
Amy Pisano: Yeah. The curiosity and critical thinking of "how could this play out" is such a huge asset.
Dale Sizemore: Trust is the currency of our business. It absolutely is. If you're trustworthy and make people believe you genuinely care, that goes a long way. A lot of people just want a quick buck and move on. If this were easy, people wouldn't need investment bankers.
Amy Pisano: Very true. When we spoke last week, you had a great story about using compliance as a due diligence tool — I know it involved Belize, which is one of my favorite places.
Dale Sizemore: I've used it in a lot of different ways. Sometimes opportunities look good on paper but aren't a good fit, and sometimes there needs to be a course correction — an expectation alignment. The registration with FINRA and working with Finalis, even if it's a debt project that wouldn't be a security, the idea is: I need to check everybody and everything out before I risk my reputation and invest my time and money in any of these projects. It's sometimes easier to say "here's the checklist that has to be done," and they may shy away from it — "no, I'm not ready" or "I see an impediment here, never mind." Some people call compliance the Department of No. But if the research shows it's not a good fit, let the process illuminate that instead of me having to tell them.
Amy Pisano: Yeah, sometimes it's having somebody put their own skin in the game and do the work — and possibly opt out.
Dale Sizemore: It's always good for everybody to have the same expectations. When they find out all the things that have to happen — all the players, the timing, everything else that goes on — it's important to have consistent expectations, shall we say.
Amy Pisano: I know you've been part of the Finalis ecosystem longer than even I have. What does it mean to be part of this kind of community, and where have you been able to connect with others?
Dale Sizemore: I'm among a handful of people who came to investment banking as an entrepreneur. I've seen what happens in an early-stage company setting out on the journey and having to adjust. It's been about four years now with Finalis and I've watched it evolve. Not everything that comes out is wonderful, but other things are brilliant. That's the entrepreneur in it — if people just stuck their flag in the sand and said "we're not changing," that would be suspicious. The evolution of Finalis, how it's going after the market, adjusting, bringing in new tools — that's comfortable to me.
One of the better things has been the camaraderie with other bankers. The ability to catch up with people and learn where to go if somebody needs help in fashion goods, industrials, whatever. Getting back to that "don't say no, but I know who might be right for this" mentality. It could be Brian, it could be Greg, it could be someone else. Having an ecosystem of like-minded people is very helpful.
Amy Pisano: Yeah. And it can be lonely when so many people are working from home.
Dale Sizemore: It absolutely is lonely. Having people who get it is both sympathetic and motivational. How do you get through it? Part of it is talking to somebody who says, "yeah, I just encountered the same thing. You're not nuts. You're right to feel that way. Have you considered this?" And then you have an opportunity to go chase that new perspective.
Amy Pisano: I'd love to talk a little bit about the market. In this current environment, what trends or challenges are you seeing?
Dale Sizemore: Anything data center and AI related — people are just scrambling to go after those. The investment community has money to spend, and in big chunks. They'd rather write one $100 million check than ten $10 million checks. So they're hyper-focused, with limited time and attention for everything else.
I see less emphasis on ESG, which was a key priority not so long ago. Oil, gas, and energy are getting a lot of attention right now. Hospitality, I'm beginning to see some softening — investors are telling me they're concerned about the impact of global economics, politics, tariffs, and currency on tourism. "We're building a hotel — does that really make sense right now?" Commercial real estate has my full sympathy. Between remote work and now AI reducing headcount, the office market is in a very difficult place.
Amy Pisano: Yes, and the impact on how junior bankers learn and develop their careers is going to be significant.
Dale Sizemore: Absolutely. I still mentor some early-stage entrepreneurs and they ask, what should I do to plan for starting a company? My suggestion: marry money. That goes a long way.
Amy Pisano: We talked a little bit about AI, but how are you using it and what are you most excited about?
Dale Sizemore: AI is a very fast-moving resource. At this stage of my life — or as I say, approaching death's door — I try to focus on the things I can use most. I use Perplexity. I like the interface, it's good for research. I use it for quickly researching and for crafting initial materials. I'll take the client's name out, make it anonymous, just a description, and get the teaser or the emails drafted. Then I put in my own validation and personality so it's not generic. I'm able to identify which funders might be right for a particular opportunity, merge the two sides, and get a document out the door. That's extremely valuable — doing more with less.
At this point, I'm going to really enjoy it because honestly, it's been the mentor I never had. I never had 20 years on Wall Street. That knowledge is now available to us if we ask it the right way. It still needs validation — yes, it can be wrong. But if I'm 90% of the way there before I finish my first cup of coffee, that is profoundly impactful for me. It's getting to the point where it rivals my cell phone as the tool I can't live without.
Amy Pisano: That is interesting, because you didn't come up through traditional investment banking, and now you have access to all of that knowledge base.
Dale Sizemore: It's kind of interesting — it's actually easier as a former entrepreneur to do investment banking using these tools than it would be to come from Wall Street and try to use AI to become an entrepreneur. Going independent means you are going to be an entrepreneur. A lot of people don't always realize how much more that entails.
Amy Pisano: It's a huge unlock for independence and scaling your own capacity, as long as you use it well and don't let it think for you.
Dale Sizemore: Yeah. I hope it helps out with medicine and law and all kinds of things in society too. But I just have to grab my little slice of the fire hose and use it in the areas I can focus on. It makes me better, helps me be more helpful to people, and it's already made me more productive.
Amy Pisano: Okay, a few quick questions to close. One tool or system you can't live without?
Dale Sizemore: AI. Perplexity specifically, because I like the interface and it's great for research. I don't do a lot of pitch decks or presentations, so I don't need the deeper generative power of Claude or ChatGPT as much — though they're great for those purposes. I'll often run the same query across multiple AI tools and compare the answers. Is there any incremental new knowledge? Do they conflict with each other?
Amy Pisano: Checking each other's work a little. A book or podcast you'd recommend to other advisors?
Dale Sizemore: I like Never Split the Difference by Chris Voss. He was an FBI interrogator. We're in the business of negotiations — sometimes it feels like a hostage negotiation — and his tips are excellent. It's easily read and easily implemented.
Amy Pisano: That is a great book. I actually took a seminar with Chris Voss a few years ago. And one piece of advice you'd give your younger self?
Dale Sizemore: Without being too pessimistic: I was raised in a generation that said sit down, shut up, go to school, make good grades, and your employers will take good care of you. That was designed for factory workers, not for reality. I would have told myself to follow the rules — I still do — but watch out for yourself more. Protect yourself. People, as well-meaning as they may be, don't always come through. Things always take longer and are more complicated than expected. Most everything has some difficulty to it. Add value where you can, build trust where you can, believe in people. Don't listen to the negative. Focus on making a contribution to people's lives, and when you die, be missed.
Amy Pisano: Yes, that's lovely. I think "advocate for yourself" is one of those lessons that usually takes getting burned once, but it's something I always try to pass on.
Dale Sizemore: Yeah, there's a delicate balance between looking out for yourself and being selfish. "Protect yourself" is different from "look out for yourself" — there's an important nuance there. Trust but verify.
Amy Pisano: Maybe "advocate" is the right word.
Dale Sizemore: Advocate is a very good description of it. Thank you.
Amy Pisano: Well, this has been so fun. Thank you for your time, and thank you for being a Finalis customer. I hope this is a lovely end to a day that started with a baby deer.
Dale Sizemore: It was nice to start out by feeding a deer — I could have even petted him — and it got better from there. It's nice to catch up with y'all. Thank you for what you're doing at Finalis. And as I said last week, if there are things you want to bounce off someone as an entrepreneur, or just another set of eyes before something's fully baked, I'm happy to offer that. If we don't give back, we don't really have the right to demand perfection from y'all. That's the only way to learn what customers really use and need.
Amy Pisano: Yes, we will definitely take that to heart. Thank you so much, Dale — hopefully we'll do this again sometime.
Dale Sizemore: It's my pleasure. Thanks again.