Becoming a VC

my commitments to founders

Interrupting this week with ~some personal news~

When I joined Boldstart in January 2021 (while still at HBS!) it was because Ed, Eliot, Shomik, and Natalie offered me as much flexibility as I wanted. Leaving a company you started is very hard and I was very noncommittal about what was coming next. I figured I'd start another one.

Today we announced our new funds at Boldstart - Fund VI and Opps III. Snuck into the announcement is a big personal decision I made nearly a year ago! I'm excited to say I'm a Partner in the new funds (and so is Shomik!)

The closest I came to an existential crisis was right before I decided to do my first deal. Up until that point, I was pretty sure I'd start another company. But a few months into my time at Boldstart I found a company I really wanted to invest in, Liveblocks.

As a former founder, I felt this weight of the decision really keenly. Your seed investor is a big deal and can have a big impact on how you feel. Especially once you get to the point of committing to join a board, you wouldn't want someone half in/half out - you want someone who is going to be there for the lifetime of the company. I was so excited to work with the Liveblocks team that I decided it was worth taking the leap.

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It's still very early days, but here are a few of the ways I'm thinking about my work so far¹. Most of this applies to people I’m working with for the long term but I tried to make some notes of how it applies in first meetings/pitches, too.

The VC you Need

A lot of founders turned VCs say they want to be the VC they wanted. I think this is no longer differentiated because many funds have former operators, and operating knowledge gets stale fast. The thing I don't love about this framing is it's pretty much explicitly saying "I'm giving advice to my past self." I don't want to look at every founder I work with as an approximation of past-me. Another way of thinking about this by imagining an engineer saying “I’ll be the PM I wish I had!” - they’d miss a lot of the other pieces of the job if they only look from that angle.

Instead, I've tried to take a stance that's a lot more like a coach. Can I 100% know what you need? Absolutely not. But I can talk to you and try to assess where you're at and show up for that.

Some of the fairly consistent pieces that have come up so far:

• When I do feel close to the situation, I acknowledge I might be biased by giving advice to my past self and they should consider it extra carefully

• Really showing up (more below)

• Pull people back to the high level and contextualize details

• Frame everything as a series of decisions that the founder has to make, then help them think through the decisions

• When something is "stuck" figure out if the founder can't, won't, or doesn't know how to make a change (h/t Eliot)

• Share potentially helpful tools, frameworks, or resources

• No matter what, be direct and kind

This list mostly apply to founders I'm already committed to working with. The same philosophy holds for new people and pitches. I want you to pitch how you are comfortable, not the way that feels more efficient to me! I want to see 30 minutes of your best - if you feel better telling the whole story, I'll listen. If you want to let me drill into one part of the product, I'll do that too. Chances are the mechanics of our first 30 minutes together won't make the difference on if I invest or not, so we should make them comfortable for you.

Really Showing Up

One thing I noticed early on is that in VC-land, your day is entirely full of meetings. A lot of the work is actually meetings. Since many of those meetings have similar characteristics (pitches, updates/checkins, board meetings) it's easy for them to feel like tasks. From the founder side, it's really hard when it feels like the VC just views you as another "to do" and isn't really there.

Another challenge is that as a VC you aren't actually doing the work. You're there to support but you aren't in it 24/7 the way a founder is. As the founder, it's equally frustrating when it feels like a VC has swooped in with a set of opinions that don't seem to take into account the full context (or worse, seem reactionary to something that happened to another company!)

Showing up and giving your perspective is a really delicate balance. I've been trying to be present and conscious about my role in every meeting. One framework I use to self-assess that is a modified version of the Drama Triangle².

VCs in the Drama Triangle / Below the Bar:

Hero - This is the role where you want to jump in and save the day (it’s also sometimes called the rescuer). For a VC "solve it" doesn't necessarily look like doing the work, but might look like a prescriptive set of advice "do X, Y, Z" or being overly in the weeds.

Villain - The Villain is also sometimes called the persecutor. They can make the other person feel small/weak for what they've done wrong. This might come out as "Why aren't you doing X?" "What made you think Y was a good idea?" or any of those horror stories of a VC yelling at a founder.

Victim - Victim is when the person feels helpless or like things are happening to them. I'd expect this to show up in an internal narrative like "why is this meeting even on my calendar?" or "why don't they listen to me?" or in an extreme "I'm going to look so bad to my partners." In a meeting with a founder it might look like sulking, resignation, or being tuned out.

These all happen. Everyone does go below the bar. The important part is being aware of what sends you there and what choices you can make to shift back up. If I hear myself saying "you should X" and feeling really committed to it, I know I might have slipped into trying to Hero. Hero is particularly dangerous for me as a former founder, because the instinct I work from now (from Lola and Dark) will atrophy and become less relevant over time.

The bottom line is that being a hero, villain, or victim doesn't help the founder or the company even if it feels temporarily satisfying. You've shown up, but you haven't really shown up in a way that will help.

Above the Bar

Coach - This is the flip side of hero. The coach provides support, resources, and ideas without getting too committed to their own ideas.

Challenger - This is the flip side of the villain. The challenger still can disagree or see flaws in a plan, but rather than blaming, they find ways to make the plan stronger. The questions might sound similar but come from a very different place. A founder would walk away thinking "wow, they really gave me some important stuff to think about" instead of "wow, they were mad at me / out to get me."

Agent - This is the flip side of the victim. The agent takes responsibility for your environment and what you can do instead of feeling helpless. Ended up in a meeting that really isn't a good fit for your fund? It's a chance to hone saving the founder time by being clear and upfront. Company you thought was going amazing now going to fail? It's a chance to figure out how to help founders on one of the hardest moments of their journey.

Listening Hard

These roles aren't just for VCs. Founders can walk into the room in one of these mindsets too (I'd give slightly different examples). You can't decide if someone is above or below the bar, that's up to them. Regardless of how a founder comes in, I want to show up as my best for them.

One thing I like about the above the bar roles is they all require listening really hard. You can't coach or challenge without understanding what's going on first. The first step always has to be listening. What happens next requires patience and feedback. Even when you're trying, you might not get it quite right. I had one call last week that really struck a balance between Challenger and Coach and we all walked away feeling great. I also had one exchange where I might have crossed the line from Challenger to Villain.

Listening really hard also applies to pitches. A founder spends thousands of hours working on their story (a lot specifically the story, and more just by working on the business). I somehow have to understand that story and if we should spend more time together within 30 minutes. This is really hard and frustrating - there’s a huge gap in trying to explain hundreds (or thousands) of hours of nuance to someone else in such a short time, and I think that causes a lot of the frustration founders have with investors. I never want to drag things out into more time unless I think there’s a good chance we might be able to work together.

#1 Fan

Some VCs work from a thesis of where they think tooling is headed. I'm not much for that. I think the frontier pushing ideas come from people who have worked on and thought deeply about one problem for a long time. Those people are founders.

It reminds me of the Oliver Wendell Holmes quote:

"I would not give a fig for the simplicity this side of complexity; but I would give my life for the simplicity the other side of complexity."

Founders are on the other side of the complexity. VCs sometimes can make a pithy statement about where tools can go, but I think it rarely has the same depth a founder would have behind the same statement. A VC with a thesis is committing to a potential bet amongst many, a founder is committing 10% of their life to one. The level of rigor is inherently different.

I also think being too committed to one idea makes it hard to see all the opportunity. If I were to spend my time to go deep enough that have that next idea, it would interfere with my ability to stay open to show up, because I'd also be holding one deep belief about what a founder should do. (A simple example of that is is that I don't angel invest in travel solely because I saw too much while working on Lola).

Instead of trying to generate "where the world is going," I love getting to be the #1 fan or "first believer/first follower" for the vision the founder has. For anyone I invest in, I believe first and foremost in them. I'd happily work for any of the people I've invested in. And secondly I believe in what they're trying to do.

If we get to work together, I hope it's like this classic video:

I can't come up with the dance, but I will surely run out out there and dance with you and start to make it real. Then I hope everyone else (more early teammates, future investors) comes to join us.

WYSIWYG

People say real me is pretty similar to internet me, so if this resonates with you, we might like working together!

• Through Boldstart I mostly invest in developer tooling, but anything SaaS/enterprise is fair game too. If you haven't started something yet but are thinking about it, I'm here for that.

• Just in how I wrote this, I already gave away at least one key thing for pitching me. The thing that gets me excited is the same thing that did when I first thought about joining Kickstarter. I want to believe in what you’re building and why it’s going to matter.

• If you're thinking about getting into VC, I can share more of the tradeoffs with operating in a future week.

• I'm still totally open for any questions Eng, Design, Product, DevRel. Send topics over! I do really want to get all my operational knowledge out there before it's useless and out of date.

1. On one hand, a year isn't very long in venture, so you should probably take this all with a grain of salt. On the other hand, a lot of my best product writing happened in the first few years of my PM career. I find 24 year old me embarrassing and I'm frequently confused about how they wrote good stuff, so hopefully 44 year old me feels the same way about this writing.

2. I got this "above the bar" concept from working with Semira. This originally comes from Stephen Karpman's work, much of which applies to family dynamics. The other roles seem to come from David Emerald. I think a lot of these concepts also come out in the book the 15 Commitments of Conscious Leadership.