What I Learned Working 2 Years at a VC Backed Startup
Hey Everyone, Dez here from All Things Venture. I’ve got some news! After working roughly 2 years at Cadre, I’ve been fortunate enough to have the opportunity to join the investing team at FirstMark. FirstMark is an early stage fund based in NYC that’s backed companies like Pinterest, Shopify, DraftKings, and more. I am super excited about this next step and to commemorate the transition, today’s article is my reflection on what I learned working at an early stage startup. Today’s article will be a little more narrative driven, but check it out and let me know what you think!
Right in the middle of Cadre’s office, there’s a gong. It sits right across one of the main conference rooms as you walk in, and it’s a mainstay of my past two years here. Pre-Covid, the gong would be rung as a reminder for the team to gather for our Weekly All Hands Meetings. Post-Covid (or however you’d like to describe the period we’re in now), it largely remains untouched - a living relic of Cadre’s history. Admittedly, I didn’t have a complete understanding of what it would be like to work at a startup before I joined Cadre. I just knew that A) I would be working on interesting, rapidly changing problems and B) I would be working in a mission driven organization (at least relative to consulting, which was my first job out of school). Startups are weird, wonderful, challenging, insightful, introspective organizations. They will leave you equal parts exhilarated and exhausted. They have the capacity to accelerate your career, and create lifelong memories and relationships. For anyone considering joining a startup, or thinking of starting your own company below are 6 of my reflections having worked at Cadre and not only seen how startups work, but having directly contributed to key initiatives within Cadre as well:
Velocity is more important than speed
Reinforce collaboration and diversity
Invest in your brand, and invest in content
Your company culture absolutely matters
Identify opportunities, articulate solutions, and execute workstreams
Remember to have some fun
1)Velocity is more important than speed
Every organization, whether they’re a Fortune 500 company with thousands of employees or a 3 person startup congregating entirely on zoom, will guide their decision making by a series of goals they’re trying to hit. What’s critically different about startups, relative to large organizations, is that the direction, the process to achieving those goals is, more often than not, unknown. This is not only part of the fun, but also the challenge of being at a startup and why I think that, velocity is more important than speed. I had to break out the high school physics textbook for this one, but velocity is defined as, “the speed at which something moves in one direction” whereas speed is defined as “the rate at which an object covers distance.” Ultimately, the right direction for every company, which contributes to the company’s ability to achieve it’s goals, is going to be wildly different and is highly dependent on the company itself. The right direction for a D2C brand selling cookware to millennials, is going to be wildly different from the right direction for AI enabled accounting software for SMBs. Either way, the point I am trying to make here is that because startups are constantly facing the unknown, and making a series of educated guesses that bring them closer to their goal, I would rather be moving in the right direction, at a lower speed than in the wrong directions at high speed. Now that’s not to say you want to stay at those lower speeds forever. There is absolutely a time and place for pouring gasoline on the fire. It’s just more effective to pour gasoline once you have a small flame going, rather than pouring it on a patch of wet leaves blowing aimlessly in the wind.
2) Reinforce collaboration and diversity
At Cadre, we had this amazing program called Cadre Chats that was essentially a miniaturized version of a distinguished lecture series but within a VC backed startup. While I was there, we had speakers like Ashton Kutcher, Darren Walker, and Margaret Anadu all come speak to us about various aspects of their careers and their perspectives on tech, finance, and real estate. It was a truly wonderful program within Cadre, but there was one Cadre Chat in particular that stood out. In one of the last Cadre Chats I was able to attend, Mita Mallick, the Head of Inclusion, Equity and Impact at Carta, came to talk with us about the importance of building a diverse, collaborative workforce. Mita shared some insight she had received/heard from the POWERHOUSE that is Carla Harris. I think Mita may have been paraphrasing at the time, but I was actually able to find a speech Carla gave on the topic . Here’s what Carla had to say,
“If you will agree [with me] that we are all in some way competing around innovation, and innovation is the dominant competitive parameter in every industry. Then you must agree, that you need a lot of different ideas in the room to obtain and retain that one innovative idea, and if you need a lot of ideas in the room, because innovation is born from ideas, you better have a lot of different perspectives in the room, because ideas are born from perspectives, and if you need a lot of perspectives in the room, you’re going to need a lot of experiences in the room, because perspectives are born from experiences, and if you need a lot of experiences in the room, you got to start with a lot of different people in the room because experiences are born from people. So to get to that one innovative idea that will allow you to obtain and retain a leadership position you must start with a lot of different people in the room.”
When you think about it more. It’s wonderfully simple. People have experiences, experiences inform perspectives, perspectives drive ideas, ideas catalyze innovation. All of us, no matter where you are in your career or life, aspire to have breakthrough moments. Creating breakthrough moments - whether it’s the birth of democracy, or the creation of the internet stems from a band of determined individuals collaborating together, BUT what we know in hindsight is that the aggregate value of those breakthrough moments, and as Carla puts it, our ability to “retain that one innovative idea” can be both expanded by and dependent on our ability to have different people at the inception of those breakthrough moments.
3) Invest in your brand and invest in content
During the last ~9 months of my tenure at Cadre, I was effectively part of the Marketing department. I helped craft our 2021 strategy, onboard key new hires, standup a strategic partnerships team, and set up our affiliate marketing program. Through that experience I would tell every early stage founder, especially if they are consumer facing, to do two things - Invest in your brand, and invest in your content. The reason why I feel confident saying this is, it’s one thing to have a great product and achieve product/market fit (And yes, I know some people will say if you have PMF the market will pull your product out of you and shoot you straight on the path to hypergrowth and an IPO), but it’s another thing to have great distribution and a ubiquitous brand. We live in a world where despite being in the throes of a pandemic, Google and Facebook, respectively have increased their YoY revenue by 62% and 56% their YoY revenue in Q2. Why? Because we are firmly living in the internet era and Google & Facebook (one can also argue for Amazon) are the arbiters and gatekeepers of internet distribution. Starting a completely new D2C brand? You’ll A/B test ads on Google. Run a product division for P&G? You’ll run campaigns on Facebook. Work at a VC backed startup? Best believe you’ll be doing both of those (if someone hasn’t already). My point is, the way you can steer your company toward more sustainable, cost-efficient customer acquisition, in my opinion, is investing in content production and developing a brand for your company that will keep you top of mind for consumers, rather than renting that time and attention from Google and Facebook.
4) Your company culture absolutely matters
As I alluded to earlier, startups are hard. They will leave you equal parts exhilarated and exhausted, so it’s important to have a strong culture within your organization that can help marshal the resources and collective talent of your organization. In 2014 Brian Chesky wrote a medium post with a beautifully simple definition of culture,
“Culture is simply a shared way of doing something with passion.”
A shared way of doing something with passion. What does that mean in the context of a startup? We’ll all have our own interpretation of his definition of culture, but I think what it ultimately boils down is this: A startup is built by a group of people. The process for building a startup is shared. Ideally, people are passionate about building that startup, but practically we all have different motivations for joining. Culture binds the individual passions and motivations for building the company, and brings them together. The interesting thing to me about culture though, is that once it’s set it can be hard to change, but it’s also something that is entirely derived from people. The habits and practices of your early employees will absolutely influence your culture, and those habits and practices persist. Aligning the culture of a company with not only the values of employees, but also with the drivers of the business can reinforce success. In a lot of ways, culture, is the sixth man/woman of startups. Championship teams don’t always need that sixth man/woman for success, but they’re in a hell of a lot better position when they know they’re there.
5) Identify opportunities, articulate solutions, execute workstreams
Ideas are a dime a dozen. Execution is everything. At a startup, there are a million things going on at once. It can be chaotic at times, but it’s also an incredible learning environment and a great way for less tenured employees to make their mark. Personally, working at Cadre was a massive career accelerant, but only because I was able to identify opportunities for the organization, articulate solutions to bring those opportunities to life, and then executing those solutions via structured workstreams. A much simpler way of saying this is, I was able to get shit done. In startups there’s less organizational bloat, so the number of hoops you have to jump through to launch a new experiment or test your hypothesis are meaningfully lower than that of established organizations. That’s not to say that you can just fire from the hip on every idea. Getting cross-functional support for your ideas will be critical not only for your personal success, but for your startup’s too. My point here is to share that, because startups are in a race against the clock, it’s important for you to be able to get things done, and get them done quickly. However, in order to do that in a consistent manner over time, you’ll need to put in processes that communicate cross-functionally not only the impact of your ideas, but also leaves room to gather input from stakeholders and leaders throughout the organization.
6. Remember to have some fun
Some of my most tangible memories of Cadre are not work related. They’re the 1:1 catchups that stretched on for 45 minutes after they ended. They’re the discussions about philosophy, cryptocurrency, and the history of the Quran. They’re the Halloween pumpkin contests that doubled as a mini talent show and costume party. They’re the goodbye dinners that stretched into the wee hours of a Thursday or Friday night in New York City. I have never been someone who thinks that work should just be about work. For many of us, we spend nearly 50% spent of our waking our hours on our job. For me, I think that time should be meaningful and align with as many of your personal goals and values as possible. It should mean that having slack conversations entirely in GIF form is totally acceptable. It should mean that having a day of culture to connect with your colleagues is not only welcomed, but encouraged. It should mean that grabbing a drink, or grabbing a coffee is important as leaving comments in an excel, or turning a deck. Will we really remember the inordinate amount of time we spend in excel? Or google slides? Or Zoom? Probably not. Will I remember the people I worked with, how they made me feel, and the memories we shared together, good and bad? Absolutely.
While by no means, are my reflections a comprehensive view of startups, I do hope that these anecdotes are valuable to anyone who is thinking about entering the startup world. I truly believe that working at a startup is one of the best work experiences anyone can have, and it reminds me of a quote from a poem by the Pulitzer Prize winner Mary Oliver that made it’s rounds on LinkedIn this summer. The poem ends by asking a short, yet thoughtful question,
“Tell me, what is it you plan to do with your one wild and precious life?”
For me, I plan on having a fun, fulfilling, meaningful life and, so far, working at a startup and being in the entrepreneurial ecosystem has contributed to that plan in tremendous way. Good luck to all of you builders, tinkers, operators, investors, and dreamers out there - let’s make something special out of this wild and precious life.
That’s it for me this week everyone! I hope you enjoyed the thoughts. Let me know what you think in the comments.
Fast forward to 27:30 in the video if you want to hear Carla’s quote
Whether you’re raising a round, or just starting to think about starting a company, I am all ears. Shoot me a note at firstname.lastname@example.org
Thanks to my buddy Brandon for spurring my original thoughts on velocity being more important than speed years ago
Thanks to everyone at Cadre who contributed to such a wonderful 2 years during a formative period in my career - the list is too long to share but you know who you are!!!