y2

Today marks two years at Redbud VC.

Whenever a big “milestone” or marker rolls around, I catch myself feeling both nostalgic and reflective. It’s so easy to get lost in the day-to-day of the calendar; there’s not much time for quiet thinking on patterns, behaviors, and decisions.

That said, I have been deliberating on what I want to share here, and I decided, in lieu of being tactical, I’m going to be a bit more spontaneous. My candid thoughts on a few themes across my 24-month tenure as an investor below.

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“Self” 

I think Emily Herrera, former VC @ Slow & Night, said it best: “You made it - which means you’re starting to think long-term about

1. What you like

2. Who you like

3. Who you are” 

This is the perfect summation of what it means to have worked in VC for two years. It is frankly exactly where I stand today. I spend a significant portion of my time thinking about those three things, and oftentimes, it feels like they’re always changing. As you start to build a circle of competence in an area, you inevitably become increasingly jaded about the value or outcome of a particular industry or trend.

Candidly, it’s weird to be expected to be a pseudo “expert” on 10 million technologies at once. Like I’m supposed to know about “application layer AI, trends in food for consumers, emerging SaaS categories, defense contracts, etc.” I think that's why Emily’s three categories are so important – they allow you to narrow your aperture for opportunities. It takes a bit of the industry-imposed pressure off.

While I’m still working on answering the above, one thing I have figured out is how to ask the easy questions. I think that good founders can smell BS a mile away, they know if the VC they are talking to gets their business or not. I want founders to know right off the bat if I understand. I often ask “easy questions” (i.e., explicitly asking “how does this work?”) and repeat information/process as I understand it for founders to correct my understanding of their companies. The questioning, coupled with the regurgitation of information, helps me not only understand the company and founder sitting right in front of me, but I believe it will help me answer Emily’s questions above.

**(Will check back to see if this is really how it goes down next year) 

Obsessive thinking 

In my opinion, the best and worst thing about being an investor is that you are always thinking. I feel always on, in a way. I like to spend my weekends taking long walks on the lakefront in Chicago. As I was walking early last week, I saw a sad little Lime scooter that had been tossed into the lake. I counted 3 Lyft bikes and 2 Lime scooters during my walk. All I could think about was how the company deals with damaged or unusable bikes/scooters: 

“It’s not super scalable to try to send a technician out to see what's wrong with them.” 

“This has to be written off.” 

“What percentage of inventory is written off like this?” 

“I wonder if anyone is building a better fleet management system for these bikes?”  

“Is that market even big enough, though?”

Yep, always on. 

The great part about this is that venture rewards unfiltered curiosity. The not-so-great part is when you’re Googling what startup makes the QR code checkout system on your restaurant table, and your friends are discussing weekend plans without you. 

Punching upwards

I love being overlooked. It’s a quintessential part of my intrinsic motivation. I’ve spent my entire life being overlooked and proving out. It would be radically uncomfortable (in a bad way) for me to be in 1st place from the start. I prefer to work to win. For two reasons:

1. There’s no pressure when you are the underdog. You’re not expected to be great. The wonderful part is that you get to work hard, hustle, and ultimately, if you're competitive, you win. No one gave it to you, and it wasn’t expected. 

2. Winning when standing at a “disadvantage” sets a precedent that you have the grit and determination necessary to win in any environment. 

When you’re junior on a team or at a small firm, you need to produce. It’s all hands on deck to do a bit of everything. Where you spend your time is critical. I realized this as I spent a better part of Year 1 getting bogged down in non-high-value tasks and the day-to-day. I’ve found the best ways to produce for your firm and your portfolio companies are: 

1. Sourcing a new company for the firm to invest in 

2. Making customer, investor, or talent intros for your portfolio companies 

3. Diversifying your firm's network of investors, founders, and LPs

spoiler: all this takes is hustle and a bit of shamelessness

At Redbud, sourcing a customer for a portfolio company is an equal win to sourcing a company for the firm to invest in. It’s easy to sell why a founder should take your money when you have examples of real value you’ve been able to add (i.e. customers).

Lost in the sauce

There’s a lot of noise in venture and startups. People are constantly sharing what they’re doing, how they’re working, and what they’re working on. (Ironically, as I do here) There’s always pressure to be doing something, which, when everyone is always talking, creates noise. If you’re not careful, you can get lost in the sauce. As I see it, the sauce is the lethal combination of natural noise, a myriad of weekly events, your day-to-day calendar, firm expectations, pressure of never missing an opportunity, the list goes on…see how easy it is to get lost. It’s essential to limit the amount of sauce you are in at any given time. I do this in 3 ways: 

• Staying focused – remembering that my job is essentially the three bullets on producing above 

• Being honest – combating the constant culture of flexing with kindness, honesty, and vulnerability, where I can  

• Having a community – a handful of investors that I share my failures and successes with, and text multiple times a week 

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It’s been a wonderful 2 years at Redbud.

To the companies in our portfolio that I’ve had the chance to be an early believer in or finder of – thank you for your trust, connection, and conviction that our small/early check would make a meaningful difference on your cap table. 

To all the founders I’ve spoken with across time zones, stages, and industries this year, thank you for your vulnerability, openness, and courage in building something new.

To Brett and Willy, thank you for taking a chance on me.