🔥The Win Game: What Happens After Everyone Has Seen the Deal?

In March, Vic Singh opened our Virtual Summit with a session on where AI actually stands for investment firms. One line from it remains critical: if every firm runs the same AI native tooling, that tooling exposes which firms have an edge.

For today’s guest episode, I wanted to double click on his statement and understand how VCs can access and win competitive deals in a world where everyone sees the same deal flow.

Vic has spent two decades as an investor and operator. He co-founded Eniac Ventures and is now a general partner at RRE Ventures alongside founding Originalis, our VC OS partner.

Beyond his own experience, Vic has run a field study on how a dozen firms win competitive allocations, and he kindly shares the learnings below in what he calls The Win Game.

Over to Vic👇

Every firm can now see the same companies on the same morning.

The databases made sure of that, and the AI sourcing tools on top of them made it faster. This is a good thing and it is not an edge. When fourteen firms see a company in the same week, the question that decides who invests is not who saw it, it is what happened next.

I have spent twenty years on the investing side of that question, as a founder and investor. This is about the part of venture that nobody builds software for and everybody lives every week: winning the deal once you are in the room and someone else is too.

I call it the win game, and my first claim is that you are always playing it, whether you know it or not.

A while back I ran a study of how a dozen firms, from seed funds to multistage platforms win competitive allocations. I talked to the people who do it. Three things came out of it that still hold.

The first is that table stakes are universal. Every firm introduces the founder to a few portfolio founders. Every firm offers a customer introduction or two. Every firm shows up smart in the room. Because everyone does these, none of them wins. They are the price of being considered.

The second is that the wins that were not table stakes were specific to the deal and the founder, and they were assembled by hand by the partner who wanted it most.

One firm sends its thesis on the category before the term sheet, so the founder knows the firm was thinking about her space before it met her. One co-signs a value creation plan with the founder, in writing, as part of the offer. One runs five distinct touches in a week, each from a different person the founder trusts. One keeps notes on every competitor it regularly loses to.

The thread through all of them is that the firm converted something only it had, its standing, its people, its record, into something the founder could feel.

The third is the one I had to learn the hard way. None of the firms I spoke to win on price. The founders who chose us over the years said the same thing in different words: I trusted this guy, I thought he would do right by me. Winning is about trust, and in a courtship both sides know they are in, if there is trust the price will settle.

Here is the thing new managers do not realize, and senior partners forget.

The win game does not start when you decide to make an offer. It starts when you lean in. If you sent the follow-up within the hour of a first meeting, asked for a second meeting, pinged a partner, or requested the data room, you are already playing. The founder noticed and the other firms in the room will notice.

Conviction is a feeling before it is a number, and the second meeting is the moment it becomes a game.

Over the years I have come to think of the right to win in four parts, and I believe any firm can write them down for any deal it is chasing this week.

The standing. What have you done in this category, this kind of founder, this geography, that gives you the right to be in the room. The companies you backed, the thesis you published, the partners who did this work before they invested in it. 

The path. Who do you know who gets you to the founder and to the people around her, and how many hops is it.

The moment. When does the round actually move. Founders say faster than it is; the person who has the founder's ear, often the lead from the last round, will tell you the real clock and what it will take.

The proof. What can you put in front of her today: references that will take the call, the plan you will commit to, the work you have already done.

If you can fill in those four lines, you have a right to win. If you cannot, you do not have it yet, and you should go earn one of the four before you spend the partnership's time.

Here is what this looks like when it works. This summer we won a competitive deal we had a right to win. We pulled domain experts the founder respected into the work before she asked. We told her the story of the own company back to the founder, sharper than the other firms in the room told it. And we reverse pitched: what we would do for the company, before any term sheet was discussed.

None of that was price. All of it was assembled in days, because the record was already kept.

The most important actor in any competitive deal is the person who has the founder's ear. Often it is the investor who led her last round. It does not have to be. It has to be someone the founder trusts, and it has to be someone who trusts you enough to tell you the truth: the range you should come in at, what you need to show her, who you should put beside her, and how long she will really take.

I have been that person on other people's deals, and I try to be close to that person on every deal I chase. The goal is more than one champion: an investor she trusts, a founder she trusts, the operator she wants.

The scenario that happens most often is the hardest one. The founder already has term sheets. She is choosing on fit and value, and terms are a large part of it. You are behind just to process the deal, and you have four working days, because the weekend counts.

This is where the unglamorous part of a firm, the system of work, decides the glamorous part. Can your memo be drafted tonight from the notes you kept over fourteen months, or does it start from a blank page. Can three reference calls be booked by tomorrow from your own graph. Can your partners read and edit the same document instead of a thread. Can IC move to Friday.

The firms that win from behind are not faster because they work harder that week. They are faster because they kept the record, and the record does the work. Their term sheets were written over weeks; yours is written from something you already had.

Sometimes you cannot catch up, and you let it go. That is a decision, not a loss, and it belongs on the record with its reason, because the pattern in your losses is the most valuable thing you own.

When you have lost three deals to the same kind of firm for the same reason, that is a finding you can act on. Most firms never see it, because nobody wrote it down.

I built software for this, so let me be honest about what it does.

It computes the four parts of the right to win from the firm's own record, and it says so plainly when one of them is thin.

It reads the heat from what the founder said, what the champions told you, and what her graph is doing in public. It proposes the plan against the room's clock, using everything the firm already has: the thesis, the references, the paths to the operator and the customer, the plan the firm can sign before she asks. It drafts all of it.

It keeps the ledger of every game, won or lost or let go, and reads the pattern back.

Take the deal you are chasing this week and write four lines. What you have done in this category. Who you know who gets you in. When the round actually moves, according to someone who knows. What you can prove today. If the four lines are full, go win it, and start with the champion. If one is empty, that is the play.

We built this into Originalis as a module called Win, because I needed it, and because the win game was the last part of my own job that ran on memory and heroics.

That’s it for today.

Thank you Vic & team Originalis for sharing a rare look at how deals are actually won. Curious how many of these patterns you, the reader, recognize from deals you have won and lost.

Stay driven,
Andre