Brian Jiang is the founder of DealDogs, an AI-powered platform that helps private equity firms, independent sponsors, searchers and intermediaries identify off-market SMB acquisition targets and likely sellers. Before founding DealDogs, Brian worked in investment banking at Greenhill and private equity at Searchlight Capital Partners. We sat down with him to discuss what proprietary sourcing actually means, why timing matters more than most deal teams admit and how lean firms can use AI without automating away the relationships that make transactions happen.
WestGate Partners: You went from Greenhill to Searchlight to venture to founder. What does that path give you sitting across from a business broker that a pure deal-sourcing background wouldn't, and what do you still have to learn from them?
Brian Jiang: At a large institution, you inherit a lot more infrastructure than you initially realize. You have the firm's brand, years of transaction history, existing relationships and partners who have been talking to companies and advisors for decades. It can make sourcing look like an individual activity when a lot of it is really institutional compounding. The long tail of the SMB market is very different. A broker, searcher or independent sponsor is often building that infrastructure for themselves from day one, so there is a real cold-start problem: Who do I talk to, why should they talk to me and how do I stay relevant over time? What I have learned from good brokers is that proprietary deal flow is ultimately relationship-driven. Technology can help you find the right people, start more relevant conversations and keep track of hundreds of relationships, but it cannot manufacture trust.
WGP: Before you'd built a single feature, what told you that off-market SMB deal flow was broken rather than just annoying?
BJ: Funny enough, we did not start with sourcing. We initially built around AI document generation, including CIMs, teasers and similar materials, and there was definitely a need there, but it also became pretty clear that general-purpose AI was going to absorb a lot of basic document creation. So we went back to users and asked where the bigger constraint was, and sourcing kept coming up. Saving a week on a CIM is valuable, but you need a deal to work on before any of that matters. The challenge was not simply finding a list of businesses. Information was fragmented, contact data could be stale and it was difficult to know which companies actually fit or which owners might be worth speaking with. A list of companies is not deal flow. Deal flow starts when you can identify the right businesses, reach the right people and create a repeatable way to stay in front of that market. Once we focused there, the reception was just dramatically stronger.
WGP: A sponsor says their deal flow is proprietary. What do you actually check to know if that's true or just a nicer word for "we got the same email as everyone else"?
BJ: I don't think proprietary search is binary. A company can be off-market without the relationship itself being proprietary, and multiple buyers can independently find the same business. I would look at whether the relationship existed before the owner decided to run a process, whether there is actually a reason that owner would want to speak with this specific buyer and whether the team can reproduce that pipeline rather than relying on one lucky introduction. Usually the advantage is some combination of timing, context and credibility. Maybe you reached the owner earlier, know their industry or geography extremely well, have done similar deals or simply stayed in touch long enough that you're the first call when something changes. Technology can help you put more lines in the water and maintain those relationships at scale, but sending someone a personalized email does not suddenly make the relationship proprietary. The human connection still has to happen.
WGP: You've talked about buyers, sellers and intermediaries all operating on different timelines. What's the most common way that mismatch actually kills a deal that was otherwise good on paper?
BJ: Everyone is working backward from something different. A buyer may have a search runway, a deployment period or a mandate and generally has the ability to walk away if a deal does not fit. A seller's timeline is much more fluid. Someone might think they're five or ten years from selling and then a family issue, burnout, an unsolicited offer or some other event changes that overnight. Meanwhile, the intermediary is often playing the longest game because a good advisor may know an owner for years before there is ever a mandate. Where people get into trouble is trying to force everyone onto their own timeline, whether a buyer pushes too hard, a seller waits until they're under pressure or an advisor hears "not now" and stops following up. A "not now" from a good owner is not a permanent no. A lot of proprietary deal flow is simply staying relevant long enough that you're there when "not now" eventually becomes "let's talk."
WGP: The ETA and search fund space has gotten a lot louder over the past few years. Is the actual deal flow keeping pace, or is more capital chasing the same off-market businesses?
BJ: There is definitely more attention and more buyer activity chasing the same pool of attractive businesses. Stanford's latest study shows how much the search ecosystem has grown, but it also shows that acquiring a company has not necessarily gotten easier: the long-run acquisition rate is 58%, while only about half of the 2021 through 2024 search-fund cohorts had acquired a business as of the latest study. The important distinction is quality. There are millions of small businesses, but there are far fewer with strong financials, transferable customer relationships, limited owner dependence and enough earnings to support the transaction a buyer wants to do. So I still think it comes back to access and timing. The opportunity is there, but you have to get in front of the right owner when the business is ready, the owner is ready and you are credible enough to actually get something done.
WGP: What's a widely repeated stat or narrative about the SMB M&A boom, whether succession wave, silver tsunami or something else, that you think is overstated?
BJ: Probably the Silver Tsunami. I don't think the demographic trend is wrong; I think people confuse the number of owners who will retire with the number of attractive businesses that will actually transact. McKinsey estimates that roughly six million SMBs could face an ownership transition by 2035, but only a little over one million are likely to be viable candidates for a sale or employee-ownership transition. A company can support an owner and a number of employees for decades and still not be particularly transferable. It might depend entirely on the founder, have messy financials, lack management underneath them or simply be too small. So the Silver Tsunami is real in the sense that there is a massive succession issue coming. I just think the investable wave is much narrower than the demographic wave, and the best businesses within that group are still going to attract a lot of competition.
WGP: Independent sponsors and business brokers are being told they need AI in their workflow. What's the honest version of what that means for a two-person shop doing a handful of deals a year, and what it doesn't mean?
BJ: For a two-person firm, your biggest constraint is usually time, so AI can be a huge source of leverage. But I would actually start with the boring stuff. If you're not e-signing NDAs, using a CRM, organizing documents properly or automating basic follow-ups, you probably don't need to jump straight to building some autonomous AI agent. Where AI gets really useful is on structured, repetitive work where the first answer doesn't need to be the final answer: researching companies, screening a buy box, organizing diligence, doing a first pass through financials or helping a broker qualify buyers. What it doesn't mean is automating every judgment or every interaction. Outreach is a great example. AI can help with research and personalization, but owners can tell when something sounds robotic. Ideally AI gives you more time to actually talk to people and build relationships. It should make a lean firm more human, not less.
WGP: You built DealDogs for high-velocity teams working the LMM and SMB end of the market. What does a deal at that size need from a sourcing tool that an enterprise-scale search doesn't, and where do sponsors get that wrong?
BJ: The biggest difference is that the further down-market you go, the messier the information gets. A $500 million company has bankers covering it, a management team on LinkedIn, institutional databases tracking it and years of readily available information. A $5 million family-owned business might have a basic website, a state license, a few Google reviews and an owner whose name appears almost nowhere. So the problem becomes much more about stitching together fragmented information and doing it across a very large universe. At the same time, I think sponsors sometimes confuse having more names with having better sourcing. You still need to narrow that universe based on what actually fits, understand enough context to have a relevant conversation and then build the relationship from there. Technology should let a lean team cover far more ground without turning the process into mass spam. That's the balance that matters.
WGP: DealDogs recently became a preferred partner of Transworld Business Advisors. What did that opportunity mean to you, and what did it teach you about building for this market?
BJ: It was a pretty meaningful full-circle moment because our first customer was actually a Transworld advisor. We got to learn from those users very early, including what information was actually useful, what workflows took too much time and, frankly, what sounded good in a product demo but did not help someone generate a real conversation. The preferred-partner relationship came from continuing to listen, fixing things, adding features people asked for and ultimately having advisors within the organization willing to vouch for us. We're incredibly grateful for that. Transworld is the world's largest business brokerage, so it is obviously a meaningful vote of confidence, but I think of it as one brick, albeit a pretty big one, in a much larger house we're building. We work with intermediaries as well as PE firms, independent sponsors and searchers on the buy side, and ultimately we want to build infrastructure that helps this whole ecosystem transact more effectively.
WGP: Three years from now, is DealDogs still selling deal flow tools, or has the product become something else entirely?
BJ: Sourcing will always be core because it is literally the top of the funnel. Brokers want potential sellers and qualified buyers, while searchers, independent sponsors and PE firms want acquisition targets. Nothing else happens until that first relevant conversation exists. But I also think a lot of good software companies start by doing one painful thing really well and then follow their users from there. The longer-term vision for DealDogs is to become the operating system for small-business transactions, helping a lean team move from identifying an opportunity through managing relationships, coordinating parties, organizing diligence and eventually financing and closing the deal. The point is not to automate the judgment out of M&A. It is to give a one- or two-person shop infrastructure that historically required a lot more headcount. People spend a lot of time talking about how hard it is to find a business, but once you buy it, you still have to run the damn thing. That's when the real work starts.
Investors, intermediaries and operators can reach Brian directly by connecting with him at brian@dealdogs.ai or visiting dealdogs.ai to learn more.