After two years of soul-searching, experimentation, and saying no to everything, I’m finally saying yes. I’ve joined Natty Zola, Ryan Broshar, and Shannon Shroyer at Matchstick Ventures. Like a moth to the flame (pun!), I’m getting back into venture capital.
That’s pretty much my news, short and sweet. However, I’ve had several people ask me how I’ve thought about this next chapter in my life (looking at you, Alex!) – so if you want to learn more about why Matchstick, and how I got here, keep reading.
What I Did During My Pause
After leaving Techstars in October 2022, I wasn’t ready to make any commitments or moves. I felt broken, exhausted, cynical, and incapable of making decisions. I needed space from venture, an industry that is broken itself. I needed to clear my head, to do nothing for a while and figure out what I wanted to do next. I promised myself I wouldn’t make any commitments for an entire year, and I estimated it would take me about 2 years to figure out what’s next. Luckily, I had the privilege of time.
In that timespan, I learned that I don’t idle well. (Who knew?! Don’t answer that.) I helped start Colorado’s first women’s professional soccer team, and I ran a 6-month performance program for early-stage founders. I traveled, biked, read, journaled, and wrote. I invested. I reorganized my whole financial world. I re-engaged as an active parent with my kids. I sit on 4 boards. I have a few consulting clients. I took a few classes (writing, coaching, AI). I ended up as busy as I was before, and I had no one to blame but myself. I have Jerry Colonna’s annoyingly insightful question in my head: “How am I complicit in creating the conditions I say that I don’t want?” Turns out, I DO want the conditions I say I don’t want. Or rather, I want what they represent. So this launched me into exploring what I actually want and don’t want.
I did a lot of reading during this exploration, but there are 2 books and exercises I’d like to highlight.
Designing My Life
The first book I read (well, re-read actually) was Designing Your Life by Bill Burnett & Dave Evans, specifically the Odyssey Planning exercise. The goal was to come up with various versions of interesting careers, each option condensed to 1 piece of paper, and include some information to help make a decision. Here is my full list, for the curious – and don’t judge – you have your own list too!
Run an entrepreneurship center
Start a gym for people over 45 (I know, Boulder, gah…)
Start a software company (at that time it was around a CRM)
Start my own venture fund
Become a partner in a venture fund
Run a B&B in a tropical foreign country
Run a cohort-based program for early-stage founders
Become a writer, public speaker
Join an existing company as CxO
Own a professional sports team
Run a 15-bedroom house on a lake with a dock and a staff, a farm-to-table regenerative farm, sustainable energy generation, and a retreat for families and startups
Launch a think tank around social entrepreneurship
Start a town (yes! I even looked at buying an existing town, no not Schitz Creek)
University professor
Start a larger-scale co-living community
After a few months of diligence each plan, I discovered that some of those paths were things I romanticised about but didn’t actually want to do. Run a B&B in a foreign tropical place? OMG bugs & laundry! This exercise allowed me to dream, to figure out what I needed to do for next steps, to figure out what questions I needed to answer, and then confidently throw out potential versions of my life without having to wonder “what if”. If you’re in a time of transition, I highly recommend this exercise.
But Odyssey Planning alone didn’t do it.
Morning Pages and Facing Myself
The second exercise was to read Julia Cameron’s The Artist’s Way, a book from the 1990s about helping artists unblock and become more creative regularly and sustainably. (A strange choice, perhaps.) The unlock for me was the concept of Morning Pages, which was to write 3 pages every day, in a stream of consciousness format, longhand. Some days, I just vented. Many days had to-do lists (insight!). Some days, I had no idea what to write about, so I just wrote “what to write about” over and over again. I wrote 3 lines of a poem once and then spent the rest of the pages expounding on what a terrible poet I was and how much I love Shel Silverstein. I wrote a scathing letter to sugar. I found myself complaining a lot, over dumb stuff. Over time, some themes emerged that allowed me to redirect my own inner voice, or realize that when I verbalized something, it wasn’t that big of a deal, or that likely to happen. I could dream freely, identify what was energizing, what was infuriating, and what patterns were on repeat in my head. Morning pages were (are) magical for me.
Between Morning Pages and Odyssey Planning – I had themes. And I wrote those out in my Morning Pages to highlight what I wanted and what I didn’t want. Here’s a snapshot:
What I didn’t want:
To be by myself, to be solely responsible.
A boss, someone I had to go along with if it was against my values, a thing I couldn’t imprint upon, or any sort of power dynamics.
To be repetitive or heavily process-oriented.
To be distant from my family, mentally and physically. I only have a few years left with my kids at home. To be a slave to my calendar, to other people’s demands.
To be around people I don’t trust, who don’t trust me.
To be one of many.
To start from scratch, again.
What I did want:
Partners, equals, people that I love, know, and trust who are values and lifestyle aligned.
To be inventive, to experiment with “how to do it differently, better”. To challenge the status quo.
To be in charge of my calendar, to spend these last precious years with my kids.
To work in a zone of genius, something I can be best in the world at (turns out, that’s working with founders)
To be on the cutting edge of technology, the world is changing too fast to be in the stands and not the arena.
To learn, to grow, to be challenged.
To positively impact the world around me, to give back what I’ve been given 10x.
This list became a decision matrix, so as I explored each Odyssey Plan, I could evaluate it through that lens. I went deeper on some of those plans (like ‘own a professional sports team, run a cohort for founders, writer/speaker) – but they were lacking for me for various reasons.
One day, Natty called me up to talk about the Techstars Colorado reboot – and it just so happened that my Odyssey Plan of “Become a Partner in a Venture Fund” page was on top next to my desk. And as I was talking to Natty, the very famous TS Elliot quote popped into my head:
“We shall not cease from exploration And the end of all our exploring Will be to arrive where we started And know the place for the first time”
TS Elliot
It became clear very quickly what move I should make.
Why Matchstick
All of the things I was looking for were right here in front of me, the whole time:
I’ve known Natty and Ryan for over a decade. We worked together closely at Techstars, so we have deep trust with each other.
I could have partners without power dynamics.
Natty and Ryan are eager to experiment, to challenge the status quo.
I can be in charge of my schedule, not have to live on planes, and be here for my kids for the next couple of years.
I can work in my zone of genius, with founders, investing in teams and helping them succeed – and this translates directly to economics for the founders, our investors, and me.
There is nothing repetitive about venture investing – each company and deal is unique.
I will be constantly learning and growing every day.
I can have a platform to be highly impactful in a positive way, not only in venture, but to startups, the people they hire, and our communities. Startups are a key leverage point for change in the world.
That brings us to today. I am so grateful Natty and Ryan are willing to give this a shot, to take a chance. Bringing on a new person in a small firm can be very disruptive, and I’m not exactly a wallflower. But I am sensitive to what they’ve built and will hold sacred what works, while helping to uplevel what can be improved. I aim to be a multiplier. I want to be one of the best in the world at this, I think I can be – and if that works, it can multiply my impact and allow me to still do some of the options in my Odyssey Plans that I haven’t yet crossed out.
So watch out world, I’m baaaack. If you are a founder between the coasts with an innovative approach to a problem or an opportunity using technology, and you have some product developed and some early signs of market interest, reach out. Let’s make something exceptional together.
Back in March, I wrote about the departure of Techstars Boulder, and on the back of the Foundry announcement, it became clear that we, as the Colorado startup community, needed to evolve and step up. For those of us who have been around a while, we remember what it was like in the early days – we knew how magical it was. People, whether representing themselves or representing different entities, got together to help the founders succeed. From mentors to law firms to CU to individuals to investors, we all participated. We were small then and could fit into one room (hello Wolf Law!), everyone knew everyone else, and we often hung out socially and had a ton of fun together. But we all had one thing in common, we wanted to help startups succeed and believed that a rising tide raises all ships.
But today isn’t like it was back then. Colorado is different. We are different. Those of us OGs are older now, there are awesome new people here, the startup ecosystem is bigger, and it needs to change and evolve. We, as a startup community, need to keep what made it magical but evolve to accommodate different times, markets, and talents.
Well, we’ve been working on just that. In part of a broader plan, I’m pleased to share that I, along with Natty Zola, David Cohen, and support from others along the way (you know who you are) have worked to launch a Techstars accelerator program experiment here in Colorado, leveraging what we know works, and trying to evolve some things that didn’t work. For example, this instance of Techstars will be locally owned, governed, and operated while still having access to the global Techstars resources. While Techstars will be an anchor investor, and David will sit on the board alongside me and Natty, the vast majority of the capital will be from the local ecosystem, governed by a local board of directors that Techstars influences but doesn’t control, with a staff that reports to this local entity. This allows the economic incentives to be fully aligned, to keep the returns and control here in Colorado, for Techstars to support the success of the local activity, and for the local program to take advantage of all that Techstars has built over the years. The accelerator has and can generate phenomenal outcomes when incentives are aligned, because when the returns are kept locally, it spins the flywheel of growing future companies here. Techstars got a lot right in the early days, and we plan to capitalize on that here, as the first community with this arrangement called Techstars Colorado, a startup community partnership.
But it doesn’t stop there, because Techstars was never the community, it was just a part of the community. In response to a ton of feedback that we need a place to gather, we are working to secure a building to be a nexus for this next generation of startups. Assuming we are successful (and are getting closer by the day!), it will house not only Techstars Colorado, but other venture funds, startups, founders, mentors, and organizations committed to helping startups succeed. We have big plans for support and resources for startups, not just at the pre-seed and seed stage, but well into the growth stages. Our goal isn’t to be the community here either, but rather to be an anchor in it, designed to live well beyond us and our influence, and to reunite the ecosystem so that we can raise the tide again here in Colorado.
It’s still early days, these things don’t happen overnight, and we will need the community (that’s you!) to step up to make this happen – which in today’s market isn’t an easy undertaking. But we have most of the key stakeholders committed and we anticipate launching sometime in 2025.
If you’re interested in getting involved, here’s what we are looking for!
Hire a Managing Partner to run Techstars Colorado (correct, I’m not running it). If you or someone you know has been a founder CEO or CTO of at least 1, ideally 2 venture-backed startups and are interested in investing, please click here for more information and to apply.
Office space or membership for a dedicated space for startups (likely in Boulder)
Investing in startups
Just would like to stay ‘in the know’
I’m excited to play a key part in uniting the startup community and helping Colorado take a key step forward in our own evolution. I’d love it if you joined us!
For the past 48 hours, I’ve been fielding texts, calls, emails, and mentions, non-stop, due to the post from Techstars about Techstars 2.0, the closing of the Boulder accelerator program and others in key cities, and the shifting of the HQ to NYC from Boulder.
Techstars has been slowly changing and adapting over the years, and yes of course some of that makes me sad. Many of the best moments of my career and life were in the magical early years there. Techstars has been such a gift, not just to me, but to all the early communities.
We all bonded not just over the mission of the company, but over its values. We lived, ate, and breathed the values of the company – and what made Techstars so remarkable was we believed we could not only create shareholder value, but instill VALUES alongside it. Everyone close to the company, alumni and employees alike, they still carry those values and work to uphold them personally. And it’s why I believe the reaction to the news has been so strong!
But Techstars needs to evolve, it needs to iterate, it needs to reinvent itself because what works on a local community level is very difficult, dare I say impossible, to pull off on a global scale. The values haven’t changed, but how they execute them has to.
I say this as I think about my daughter who is turning 14 shortly, and is one of the reasons I left Techstars back in 2022; I wanted to spend more time with her before she leaves for college. When she leaves, I will be indescribably sad, unbelievably nostalgic, but also incredibly proud of her as I watch her reinvent herself, as I watch her evolve and grow. She’s going to leave ‘home’ in search of her next chapter, but her roots will always remain here in Boulder, here with me. And when she leaves, it’s then time for me and my husband to reinvent ourselves too. For everything, there is a season.
So go Techstars, go reinvent yourself, go create the 2.0 version that kicks the 1.0 version’s ass. Thank you for all you’ve given us, for showing us what’s possible, and for paving the way. Please keep spreading those values far and wide, and remember always where you came from.
And for all the communities that feel vacant now – it’s a chance for us to reinvent ourselves too. We can reignite that entrepreneurial spirit that’s true to our communities and not in service of anything else. We’re already working on it in Boulder.
If you want to go fast, go alone. If you want to go far, go together.
African Proverb
I’ve always loved this quote.
Last week, I kicked off a program for venture-backable early-stage founders in Colorado. I have 14 CEOs participating in 2 groups that meet every other week for 3.5 hours for 6 months. This program was designed to help them go farther together and is an experiment I’m running to see whether or not the framework I’ve developed can help them move the needle on performance.
That’s 14 founders of startups who believed in what I’m trying to do, who signed up for an experiment that takes significant time and effort on their part, with no guaranteed outcome. When I let myself think about it, it’s humbling, daunting even, and I feel so incredibly lucky and grateful to have pulled such a winning lotto ticket.
This effort is the culmination of a lifetime of stars aligning, 20 years of professional experience, 10+ years of rumination, and 4 months of running at it as hard as I could. But really, it’s the culmination of a network of people who have helped me go far, rather than just go fast.
I’m not going to talk about the program today, rather, because I’m feeling sappy, I just wanted to take a moment to sincerely and publicly thank those who have been so helpful these last 4 months in the background. May we all have those who help us get farther than we ever could alone.
If you’re an entrepreneur interested in raising venture capital, or maybe you’re an individual looking to get into venture capital, I cannot recommend this course enough. When I was learning venture, the book Venture Deals was my bible, and luckily I had the authors Jason & Brad to call as friends. Now it’s been turned into a free course thanks to the effort of the Kauffman Fellows and Techstars, and I was honored to be included as part of the team.
The course starts on February 22nd, and it’s free – no strings attached.
I recently gave a talk to a room full of founder/CEOs about how to leverage your board of directors by shifting from a reporting board to a collaborative board. It can be tricky, but for those who do it, the company and the founder can grow wings. Part of the shift involves trusting your board and bringing them into your confidence, being vulnerable with them, and asking for their help and input when things aren’t working. This can be scary for most CEOs because the board usually has the power to remove him/her. However, if you have the right board members, and if you create the right dynamic at the board level, this usually won’t be the outcome.
One founder in the room raised his hand to challenge me. He said, and I’m paraphrasing here, “That’s a lot of ifs and usuallys. Why would I take that risk? If my board can fire me, why would I risk being fired and losing my company by admitting weakness and vulnerability?”
I love this founder for asking that question – it’s at the heart of why most CEO’s don’t go to their board with challenges.
Here’s the thing: There’s a difference between playing to win, and playing to not lose.
Let me tell you a quick side story. I played volleyball in high school and club ball in college. I’m short, so was never going to be really good, but I loved it. My freshman-year dorm was across the street from a frat house with a sand court in the front yard, and I was dumb enough to ask to play with the guys who were much taller and more skilled than I was. They were nice enough to let me participate, and for a whole year I spent every day after school and all my weekends there. Eventually, I got good enough to hold my own, and we competed in a few sand tournaments. I never won, but placed decently, and even taught the volleyball class at the University for a while.
Fast forward 20 years, I started a couple of companies, had a couple of kids, moved a couple of times, and made 100+ investments, raised a couple of funds, traveled an inhumane amount, had a ludicrious number of direct reports, helped grow Techstars… basically, I had zero free time to do things I loved like play volleyball.
So recently, I decided to pick it up again. I found myself on a co-ed, indoor sand team. I was pretty nervous to start, but hey, I’m decent at this sport, so I figured once I got my legs under me again, I would be okay. Well let me tell you – I was bad, so embarrassingly bad. I shanked every pass. Put every attack in the net. Dove and missed every ball. Lost every overhand serve. It was so bad that one teammate asked me to serve underhand, a big hit to my already fragile ego. It’s been a long time since I felt that humiliated. We lost every game that season and were relegated to the lower league, largely because of me.
Astonishingly I was invited to play the next season (I’m 100% sure it was because they couldn’t find anyone else), so I swallowed my pride, said yes, and started practicing, figuring my ego needed to practice sucking in public. Luckily I got better and better. I wasn’t anywhere near as good as I was 20 years ago, but at least I wasn’t an embarrassment anymore. Yet I continued to serve underhand – because I was so afraid of losing the serve. A killer overhand serve will earn you points, but a bad serve will earn the other team points. You can win whole games on a killer serve alone. When I practiced, my overhand serves were killer. They were strong and hard to return and my team kept asking me why I wasn’t serving overhand in the games, but the truth was I was afraid to choke. I didn’t trust myself anymore and I didn’t want to cost us the game. I was playing to not lose, I was not playing to win. Despite my conservatism, our team placed #1 in that division and got promoted back up to the higher league, but, I didn’t get invited back to the next season because I didn’t help win games. I just helped not lose them. And quite frankly, I don’t blame them; they wanted to win.
This founder’s question is like my underhand serve. It’s playing to not lose. And when you’re in the high-stakes game of entrepreneurship, especially if you’ve taken venture capital, there are only 2 outcomes, winning, and losing. So if you’re playing to not lose, you will likely, eventually, lose.
Here are common behaviors I see founders take that show they are playing to not lose:
Not being honest with the board
Stacking the board with friends rather than skills/knowledge/wisdom/networks/courage/honesty
Not asking for help
Trying to be good at all things
Not having a difficult conversation with a co-founder, leadership team member, investor, yourself
Not asking for feedback
Dismissing other people’s feedback
Needing to win disagreements
Not hiring people smarter/better than they are
Hiring up, and scaling up before true product / market fit
Trying to raise more capital because you hired/scaled faster than you should have before you have product market fit, and you’re now out of runway
Trying to keep the business alive when there’s clearly no real business, and burning through all the investor capital without returning any of it
Not making a major decision
Micromanaging, not trusting your team
Using policy as an excuse or crutch for not developing judgment
There are infinite ways that playing not to lose manifests but at its core is fear; fear of failure, fear of loss. The trouble with this behavior is that it almost always manifests that which you are exactly trying to avoid. For instance, not being honest with the board will eventually lead the board to not trust you, which will either cause them to not vote with you or they will try to remove you as the CEO. It just takes longer, but in the interim, you’ve burned all the bridges and not gotten the help, trust, and support you needed to turn the issue around.
Don’t mistake playing to win as ruthless, win-at-all-costs actions; that simply isn’t true either. You might win a battle, but you will eventually lose the war. Playing to win does mean taking risks, but it means taking calculated risks intentionally, collaboratively, and intelligently. In the land of startups, a win-win-win outcome is possible because together you can create more value than you othewise could apart.
Here are excellent playing-to-win behaviors:
Recognizing your weaknesses and staffing for them
Asking for help, asking for feedback
Admitting a mistake, asking for forgiveness
Build and manage a board of directors that can be as influential as your leadership team
Make a hard decision, even if unpopular
Hold people accountable, especially yourself
Taking a big swing, that’s calculated, intentional, aligning, and collaborative, with tailwinds
Having a scary conversation with someone
Conserving every f’ing penny until you have product market fit
Keeping your day job/not raising money until you have product/market fit
Shutting the company down and returning capital to investors when you can’t see how you’re going to make it work
Saying NO to distractions
Being generous with equity with the *right* co-founders, employees, investors
When people disagree with you, get curious, not defensive
Investing in your own professional development
Identifying the one thing your business can be best in the world at, and going hard at it. Don’t make marginally improved products/services.
Recognizing when you aren’t best suited for your role in the company anymore
Of course, all of this is situationally specific, and the true answer to any question is “It depends” – but I ask you – are you playing to win? Or are you playing to not lose? Are you serving underhand? Or overhand? What can you do or stop doing to shift to a winning orientation? I encourage you to ask that question, not only of yourself, but together with your team and your board. “What could WE do, or stop doing, to help us shift from playing to not lose, to playing to win”. What a powerful way to reorient and kick off a new year.
Special shoutout to my friend Ari Newman, Managing Partner at Massive who served as an editor, contributor, and sounding board for this series.
You’ve come so far, my friend! You’ve got yourself in the right headspace about how your board is your not-so-secret weapon, you have the right people on your board, you’ve established a highly functional, productive, and trusting relationship with them, plus you’ve created a killer board package. Now it’s time for… dum dum dummmmm, the meeting. In all honesty, once you’ve done the above things well, the meeting is the easy part.
This is part 3 of a series around navigating your startup’s board of directors. It focuses on the board package, what documents and sections to include and how to organize it. If you haven’t yet done so, please read Part 1 – The Framework and Part 2 – The People.
Special shoutout to my friend Ari Newman, Managing Partner at Massive who served as an editor, contributor, and sounding board for this series.
Applications for Techstars in Boulder are open, and to celebrate, we’re hosting a cadre of events that are valuable and full of tactics for your startup. We love helping entrepreneurs, so it’s free and open to the public. Last year, we called it 7 Weeks of Awesome, and we got such a positive response, we decided to do it again, but more awesome! This year, it’s 8 Weeks of Awesome, every Tuesday for 8 weeks @ Techstars in Boulder. Please RSVP below.
Nearly Nicole 