Nghi Tran is a Fund Manager with Big Red Ventures, interviewed Mr. Jeffrey J. Koh, M&A and VC Partner at Reitler Kailas & Rosenblatt LLP in December 2025.
Nghi Tran: You sit in a very rare seat in the venture ecosystem: you’re an M&A and venture partner at one of the top 10 VC law firms in the U.S, advising leading funds, founders, and operators. I’m really interested in how you read people, how you read founders, how you think about compounding decisions, and how you make judgment calls when the stakes are real, especially given that you often see companies at their most consequential moments.
Nghi Tran: A lot of this becomes clearest when deals are under pressure. When a deal is close but not quite there, what usually determines whether it moves forward or stalls?
Jeffrey J. Koh: In the context of an M&A deal, one entity wants to buy and one wants to sell. Some people approach the negotiation as zero-sum, buyer gets one more dollar, seller gets one less dollar.
In reality, there are dozens of negotiable points. What really matters is deal leverage: who wants it more and who is more willing to say yes across multiple dimensions.
Most of what I do is in the context of negotiating a deal. What I often do is I take the deal points at any point in the deal. As you go through the deal, there’s ~ 20 points. I rank them. You can assign a fake net present value to each deal point in terms of importance.
Instead of treating every point as equally critical, I rank them in reverse order. Maybe there are ten points that really matter, and ten that don’t. Those lower-priority points become trade-offs things you can give up to protect what truly matters. That framework is how I advise clients through M&A negotiations.
As you move earlier-stage, the role shifts. It becomes less about negotiating every point and more about stepping back and asking: if you’re going down this path, what are the few things you really need to get right?
If something isn’t a sound idea, the challenge is balancing respect for the founder with the responsibility to say, “Here’s how I’ve seen this go wrong before.” Usually, you have to build rapport way before that decision. You don’t want to be building credibility for the first time when there’s already a problem. Without that history, it’s very hard to deliver that message effectively.
Nghi Tran: Right, credibility. When you say you prioritize your clients, how do you decide when to really push for what they want versus when it makes sense to be flexible so the deal actually gets done?
Jeffrey J. Koh: If I’m representing a founder, it’s usually sell-side where they’re raising liquidity. It could be they’re selling 100% of the company or a significant stake, they’re raising a round. What a seller wants, in some kind of order, is pretty consistent.
If it’s a control deal, there’s closing certainty. You want to make sure this horse in the race will get you all the way to the end, because you don’t want to negotiate with the wrong one. So you determine, does this person have the money, do they have the ability to get the deal done.
Then there’s price certainty. You want to make sure the person’s actually paying what they say they’re going to pay for the business.
Beyond that, there’s indemnity and downside protection. In VC deals, usually the sellers have a limited set of representations. But in control deals, there might be some liability, so the seller can’t just take the money and go to the beach because they might be worried about a claim from the buyer later on.
Then there’s control and consent and veto rights and board rights. The founder wants to take that money, and if they’re still in the business, they want to run it the way they want.
Those are the priority areas when you’re selling a company or raising liquidity. Any deal point becomes, how do I maximize those things for my client while still trying to win the deal?
On the buy side, there’s a different set of things the buyer cares about. I think sometimes people get into the weeds and negotiate each point. For each point, it’s important to have the perspective of, why are we fighting over this? That determines how hard you fight. If it doesn’t maximize my client’s main goals, we might trade it for something else. But if it impacts those key goals, then we want to hold that deal point.
Nghi Tran: Let’s pivot to early‑stage companies. I’m sure you’ve seen thousands of cap tables. What are some decisions early‑stage founders consistently overlook in structuring ownership that come back to haunt them later?
Jeffrey J. Koh: Yeah. So I always say, never, never, ever give up equity unless you really, really have to. And then even so, think twice.
Equity is so expensive. The more the business grows, the more expensive it becomes. Founders are often tempted to say, “We don’t really have anything right now, so instead of giving you real money, I’ll just give you a percentage.” If the business succeeds, that percentage ends up being worth a lot more for everyone. Raising venture capital, giving up equity, doing anything with your equity. You’re essentially giving up a percentage of your life and the thing you’re working on.
As a lawyer, I’m happy to document the next Series A. Great, let’s do it, it generates work. But the person with the idea needs to be very careful about how they parcel equity out.
I can’t tell you how many times a founder asks me, “How many percentage points is this worth? How should I structure the cap table? How much should I give up?” And I always say: model it out. If this becomes a $10 million company, a $100 million company, here’s what that percentage actually means and here’s what you keep.
There are all these beautiful graphics about what’s the market standard for Series A: how many percentages the founder keeps, the employees, the lead investor, the advisors. There’s so much data for similarly situated companies and what their cap tables look like.
I always tell the founder, you should focus on your idea: build it out, generate value, go do the thing. But it might be worth spending a couple of hours with me or with cap table math, where you take the model just so you’re crystal clear on who owns what and what the tax consequences are. Tax drives a lot of it.
Just spend a couple of hours with someone who’s done this a hundred times. As you’re building, as you’re handing equity out, as you’re bringing people onto the team, understand at each stage what you have and what it’s worth. That clarity really matters.
Nghi Tran: Say a founder is building an early‑stage company. There’s been a huge rise of fractional CEOs and CTOs. From an investor perspective, does bringing on a fractional C‑suite signal maturity and self‑awareness, or does it raise concerns?
Jeffrey J. Koh: Yeah, that’s a good question.
Ultimately, the buck stops with the founder. But the reality is that founding a business requires many different skill sets. It’s a lot of jobs rolled into one.
It’s building your idea, making the widget. That’s the most important part. But then there’s fundraising, which is a whole different job. That’s a full‑time roadshow kind of job. Then getting the books in order, making sure your P&L works, accounting, and how the finances are presented.
AI kind of changes this a little bit because a lot of the rote stuff can be managed and delegated. The way I think about the fractional piece is:
First, the founder needs to understand what standards they need to hit at each stage. What a pre-seed company should look like. What a seed company should look like. What it takes to be Series A ready.
Second, the founder has to honestly evaluate their own strengths. Maybe you are strong with numbers. Maybe you are great at talking to people. Maybe you are excellent at building the product. Not everyone is strong in all of those areas at once.
If you’ve done those two steps and you’re delegating the part you’re weak at, I think investors would see that as mature. That is very different from saying, “I do not want to deal with this, so I will abdicate responsibility, slot in someone fractional, and forget about it.”
The better version is, “I know what a modern, professional company raising venture money should look like. I know my strengths, and I have brought in help to cover my weaknesses.” That is a very mature signal.
A lot of founders from zero to one have taken on all the different aspects. They find it a little bit hard to let go. Being able to strategically ask for help and delegate different pieces helps you scale. It puts you in position to scale and bring in more help and grow your operations.
If a founder frames it as, “This is how I am addressing my weaknesses and preparing for scale in ways I cannot do alone,” that is a really good sign for investors. You have to be intentional about how you present it.
Nghi Tran: I agree. On the flip side, I’ve noticed that fractional roles can mean very different things in practice. Sometimes that reflects real leverage, and sometimes it is more about signaling. How do you tell the difference?
Jeffrey J. Koh: Right. Delegating is hard. Actually empowering that person and letting them build a portfolio.
It doesn’t work if you delegate something to someone and you don’t empower them. What happens then is two things: First, they only deliver an 80 percent version. Second, the time it takes you to review, verify, and correct their work often ends up taking more time than if you had done it yourself.
That model doesn’t work. You have to empower someone enough that the work truly comes off your plate. When that happens, the time you spend reviewing becomes a fraction of what it would take to do it yourself, and that frees you up to focus on other things. Otherwise, you are stuck teaching, coaching, and verifying, all at the same time.
That is also where AI can slot in well. It does not replace the thinking, the judgment, the aesthetic, or the responsibility of making sure something is right. But AI does take away a lot of the grunt work. You can ask AI to do 80 percent of the work, and then your role becomes verifying, editing, and refining.
What you cannot delegate is inspiration. You cannot delegate the core thinking about the idea or the act of building something meaningful. From my perspective, anything that helps a founder spend more time on that is a good thing. Founders should be focused on the inspiration and on creating value. Everything else should exist to support that.
Nghi Tran: That is a good use of AI. While it saves founders time, it can also create false confidence. What’s your take on that tradeoff?
Jeffrey J. Koh: Yeah, think of it like a super hardworking, but drunk intern. You ask it to do something, you get a lot of good data, but you have to verify the output.
If you approach it as, “This is the drunk intern who made this report for you,” that is a good way to guard against false confidence. We now have almost unlimited capacity and access to information, depending on the data source. But the real question is whether it sorted the information correctly and whether it presented it in the right way.
You still have to verify. The mistake I see is people blindly trusting the output, and that is where things go wrong.
Nghi Tran: Stepping away from technology for a moment. You work with more than 50 search funds, which gives you a front-row seat into how operators actually lead when they take over a company. What surprising patterns have you seen in companies acquired through search funds?
Jeffrey J. Koh: Search is an interesting world, especially alongside VC.
In a traditional search model, you typically have someone coming out of an MBA program who is backed by a group of search investors. Together, they go looking for a very specific type of business to acquire.
Search investors and search boards tend to be more actively involved than a typical VC board. That is partly by design, because the person stepping into the role is often young and has not previously run a business. You are essentially taking a 26-year-old, 28-year-old, or 30-year-old, having them buy a family business, and expecting them to learn how to run it.
It has gotten quite saturated. A lot of search funds are chasing the same targets. The more cynical view is: of course, if you buy that kind of business, you have already stacked the deck so much financially that you can grow it with only minimal operational improvement. That is part of why you can put a 28-year-old in the role, because a portion of the outcome comes from financial alchemy.
The less cynical view is that because that ecosystem is so intertwined and so close, there are a lot of people who’ve done it before that are around you that can give you advice. That ecosystem, the different conferences, the different search investors, the boards, the various portfolio company CEOs, is all really friendly in terms of telling you what to do.
I will say, because of that, having operational experience is quite valuable. There are a lot of deal guys, but less operators. I have been in board meetings where the new owner is clearly learning on the job. For some, it goes very well. For others, there is a moment of realization that they are now truly running a business. It is certainly interesting to see
Nghi Tran: Both with early-stage VC and with search, it sounds like you’re really betting on the person. What are the qualities people say you should look for in founders that, in your opinion, we over or underweight?
Jeffrey J. Koh: First, in the US there is definitely a bias toward extroversion. People who like talking to others, going to events, and being visible tend to stand out. That can be useful for fundraising, and you can probably draw a line to PR, building a customer base, and generating momentum around a company.
But it’s unclear you can draw a line from extroversion to being successful at building and scaling. We probably over-privilege extroversion.
At the same time, we tend to underrate qualities like simply being a good person, being socially motivated, caring about your community, and being genuinely likable. That is also hard to evaluate in a short interaction. It is difficult to assess whether someone is truly a good person, but I think that quality is undervalued.
The third trait is the ability to handle adversity. Having conviction in the face of setbacks and continuing to push forward matters a lot. Whatever happens, you keep going. That is probably the most important trait of all.
In sum, those are three: Being socially impact‑driven is underrated. Extroversion is overrated. And getting after it is very important.
Nghi Tran: As a final lens, you’ve lived through complex geopolitical realities and now advise founders in the US. How does your background shape how you see risk, especially for companies with an international approach?
Jeffrey J. Koh: I would say Venture is very US-dominated in terms of people investing. New money moves fast. Old money is conservative.
You can roughly map that distinction onto US and European venture markets. Asia feels more like family offices.
What I have seen among many of my friends in venture is a simple pattern. They take an idea that works well in the US and ask whether there is a comparable market elsewhere. In some cases, particularly in tech, parts of Asia may be several years behind in adoption. That creates an opportunity to adapt or localize a proven model and build something successful.
In many ways, Silicon Valley still sets the tone. A lot of market practices originate there, and then get mapped to other regions. There is often a real opportunity for people who study what is working in San Francisco and apply those lessons thoughtfully in their home markets. That approach has proven to be quite lucrative for many.
Nghi Tran: This was an incredible conversation. Thank you so much for sharing such candid and thoughtful perspectives. I know the BRV community will take a lot away from this. I hope you have a great holiday break ahead.