I’m sitting in Avanti, adjacent to the Boulder Theater, hiding in a back corner because I can’t seem to get a quiet, undisturbed spot to write this post. Downtown Boulder is filled with Techstars people here for Foundercon: alumni, executives, staff, mentors, and previous managing directors. I can’t walk 5 feet without seeing someone I haven’t seen in years. On Monday, over 30 ex-Managing Directors, unofficially called Techstars Mafia but officially called the Techstars MD Emeritus, gathered to share tips and help each other grow our funds (most of us run funds now, with a few operators and 2 bankers). It feels like déjà vu. With David Cohen back as CEO, hopeful, cautious optimism is the shared sentiment, with a sprinkling of other complex emotions for this org that we all loved. Love.
Shay (pronounced shy, but he’s definitely not shy) has raised capital, built teams from scratch, scaled products to millions of users, and experienced both the highs and lows of startup life. As Managing Partner of Techstars Boulder, he’s focused on helping founders navigate those same challenges — from finding product–market fit to building resilient teams to scaling without losing their edge. He brings both deep operating experience and strong ties across the startup ecosystem, here in Colorado and globally.
Most importantly, Shay is deeply aligned with our mission to keep Techstars rooted in this community while evolving it for what founders need today. He believes, as we do, that when incentives are aligned locally, we can spin the flywheel of growth and opportunity for the next generation of Colorado startups.
You will see a lot of Shay in the coming weeks, months, and years. Please help me welcome him to the role. Wrap your arms around him. Ask him “how can I help” and support him as he works to build an accelerator and community that reflects the best of Colorado’s startup spirit.
This is just the beginning, and we’ll have more to share soon. In the meantime, if you’re interested in getting involved as a mentor, investor, sponsor, or member of our future space, sign up here.
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!
I have sat on many boards of directors, and since many, dare I say most, have been mediocre at best, I’ve become passionate about how to make them highly functional. Because of this, I recently had a conversation with a founder CEO, let’s call him, Joe, who asked me how to get rid of a particularly problematic board member, let’s call him Alex.
“Well, I need more context. Tell me about Alex” I asked Joe, the CEO.
Joe replied, “Alex used to be an ideal board member. He read all the materials in advance, he came prepared to the meetings with thoughtful insights, and he debated appropriately. He made a handful of high-value introductions and helped me think through some major issues. Alex was one of my best board members1”.
“But recently, Alex’s behavior changed drastically—arriving late, being combative, asking questions we covered 15 minutes ago, and spending board meetings on his phone. He yelled at me during our last meeting, making things intolerable. What’s the best way to fire him?
I responded, “Have you asked Alex if he’s okay?”
Blank stare from Joe.
“You know”, I continued, “Since Alex previously was one of your best board members, what has changed? Why is he acting this way? Have you just asked him if he’s alright?”
Joe kicked an invisible pebble with his foot and sheepishly admitted he hadn’t.
We’ve all heard how important company values are; they are the basis of the culture of our company and we spend hours upon hours writing them, agreeing on them, training on them, hiring against them, and putting them on walls. And secretly (or maybe not so secretly), we all roll our eyes and know they’re bullsh*t.
Here’s why.
Most companies put up aspirational values – ways they WANT the team to act – ways they aspire to behave. But for every minor infraction of those values, every time a leader doesn’t act in alignment with those values, it immediately discredits all of the values, all of the time. Employees immediately know the values statements are just lip service because even the leaders aren’t following them. Yet how can a leader align with an aspirational value 100% of the time? It’s impossible. I aspire never to yell at my kids, but the 314th time I’ve asked for the dirty underwear to be picked up – I’m probably yelling it.
Values aren’t something you choose. A person’s values form slowly, throughout their life, and they are reflective of how the person actually acts. Values manifest in your behaviors, not in your words. You can’t choose them from a list, you can’t ship them over to marketing for wordsmithing. A company’s lived values are reflective of the founders’ personalities and how they behave, or if the founders aren’t there anymore, the CEO and executive team’s behaviors – and rarely are they the same as the company’s stated values.
If you say transparency is a company value, and you don’t share the board deck with the employees, boom, values shot. If you claim ownership as a value, but there are 4 layers of decision approvals, boom, values shot. If you claim constant improvement as a corporate value, but have zero mechanisms for doing retros on all decisions and actions, or rarely make changes to your processes, boom, values shot. Values have to be reflective of how you actually act, not how you want to act.
That doesn’t mean you can’t have aspirational values. I think it’s phenomenal to have 2 sets of values, 3 actual values, and 3 aspirational ones. But distinguish between them so everyone knows what you’re trying to do and how it is today. Otherwise, it’s total bullsh*t.
Since the company’s values tend to reflect the founders’ or the CEO’s values, it’s important to know what those are and use those as a foundation for the company. The trick is that you as the founder probably don’t know what your values are, because it’s just in how you behave every day. But everyone else can see them. If you want to do a values exercise, try this. Brene’ Brown has a great values worksheet. Fill it out for yourself, but then ask 5-10 people closest to you to fill it out for you. Ask them what they believe your values are. Your values are likely the ones the respondents identified and overlap. Have your co-founders do this same exercise, and the 3 or so respondent-identified overlaps between the co-founders are probably the right ones.
There’s something magical that happens when the right values are identified and listed. It’s like a collective exhale. The founders and leaders are acting in integrity with the values all the time, and the rest of the team now knows how to behave. And you really can start hiring for it, promoting for it, and using it as a guide to make decisions.
May 13th kicks off the 15th annual Boulder Startup Week 2024 – a volunteer-organized weeklong celebration and conference for startups in Colorado. It’s a free event (thanks to all the generous sponsors), with over a hundred sessions for every topic important to startups, and is designed to include anyone who wants to participate, while engaging the entire entrepreneurial stack.
Almost everyone I know in Boulder will be participating in some fashion, whether it’s presenting, attending, hosting, or sponsoring. The energy around town is palpable! There is a ton of great content, something for everyone so make sure you look through the whole schedule, and if you don’t see something that suits you, just come hang out. Serendipity is a powerful force when you put yourself in it’s flow.
I’m hosting 2 events and on 2 panels, so come find me:
And on the unofficial schedule (and shameless plug), on Friday after the happy hour, we’ll head over to the St. Julien at 6pm for a free concert by Peak2Peak – my husband’s band who does mostly Grateful Dead covers. Hula hoops and tie-dyes welcome, live music for the win!
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 was at an event recently where one of the sponsors took about 5 minutes to address the room, talk about his firm, what they offered, and how to reach them.
The crowd politely clapped, as everyone usually does with sponsors, but I seriously doubt a single person from that event will reach out – not because he did anything wrong, but rather because there was no value in what he said. Having been in the event organizers’ position of relying on sponsor dollars to make the numbers work, I was bummed for all of them. And it got me thinking about the notion of value. At Techstars, we had a word for this, it was called #GiveFirst, but in my mind, it’s not just about giving, it’s about adding value first.
In the early days of Techstars, we didn’t yet have a lot to brag about. I could show a few logos, sure, but like any embryonic company, you’re trying to figure out anything you can say to gain credibility, to gain attention. I remember trying to recruit companies for Techstars and David Cohen giving me the sage advice to teach people something, rather than just waving a banner.
Oh, the wisdom in that guidance. Rather than just posting about applications opening (which I did with little effect), rather than just asking every person I knew to refer companies (which I did, with little effect), rather than taking out ads (which I didn’t do because I hate ads and we didn’t have the budget), I just started hosting free talks. It was always about something startup-related, and often I didn’t even lead them, rather I got someone else a lot smarter than me to do it. I just promoted it. For instance, Jason Mendelson on “20 ways to f*ck up your company”, or Paul Berberian on the hilarious Zenie bottle story, or Matt Blumberg on how to be a CEO. It was usually an hour long, and I always ended it with “and Techstars applications are open until X – if you have any questions, I’m here and would love to talk to you about it”. The key was the talks were GOOD. They were educational, from people who knew what they were talking about. And when event attendees saw this small show of value, they could imagine what a whole accelerator program might be like. I often spent sixty minutes or more after the talk answering questions for people interested in the program. And so the flywheel of marketing began to turn. That piece of guidance was a huge driver of the early success of Techstars.
Fast forward a bunch of years, and the same thing happened with Digital Ocean. They were in their infancy, were a cloud hosting provider up against complex behemoths like Amazon, but had some very lofty growth goals. Digital Ocean was proud of how few clicks it took to set up a web server on their hosting platform relative to Amazon which could take hours to figure out. Taking a page out of “add value first” – they followed some sage advice from Jason Seats; rather than buying ad space, they created a bunch of how-to articles including a lesson in how to set up an Amazon web server without errors, literally helping people be successful on their competitor’s platform. However at the very end of the post, they said “…and if you don’t want to do this work, check out Digital Ocean”. What I loved about this approach was their main focus wasn’t promoting Digital Ocean (although they hoped that they would get customers out of it). Their main focus was making someone else’s life easier. They eventually IPO’ed, the roots of adding value embedded deep within the fast-growing company.
Companies spend billions of dollars a year trying to get our attention, such as all the ads we are subject to, or that sponsor who paid good money for brand recognition and 5 minutes on a stage. We are so overrun with this noise, that we tune it out – and the response of the marketing departments is to spend MORE money, say it louder, say it more often, creating more noise and making us filter it out even more. It’s a vicious cycle of absence of substance.
If you want to get someone’s attention, try adding value first. The trick is that value is in the eye of the buyer, not the seller, so you really need to think about what your audience values. Taking out advertisements to tell me how awesome your CRM is doesn’t add value to me, even if I need a CRM, because every CRM is doing the same thing, so it’s just more noise. But taking out an ad to market a free class or video on how your CRM syncs bidirectionally and seamlessly with no code to that spreadsheet my intern uses, and then giving me a month free trial for taking the class? Love it.
Consider setting up a challenge in your company for your marketing team – ‘You aren’t allowed to market. You are only allowed to teach – even if it’s teaching about how to use a competitor’s product’. How about co-writing a blog post with an investor about some challenge your business is facing, and letting that investor publish it on their website? The ideas are endless, you just need to think creatively.
Adding value takes thinking outside the box, I dare say it’s applicable in everything you do, and when you get it right, people will trust you more. Your customer base will be more tightly vetted, leading to happier customers with longer LTV. Your investor will be more likely to fight for you and bridge your next round when things aren’t going as planned (and let’s be honest, they RARELY go as planned).
Challenge yourself to find a way to add value in every interaction. You’ll end up with a tidal wave of support that lifts you higher and propels you farther than you could ever imagine.
Nearly Nicole 