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Friends,

If you work in tech, there’s a good chance you’ve heard some version of this sentiment: you’re the average of the people you spend time with. Fritter away your afternoons with unambitious dawdlers, and you may soon find yourself lowering your sights; surround yourself with passionate, driven people, and you will be forced to raise your game. 

Even exceptionally driven people can be knocked off-course by external influences. A young Warren Buffett, for example, found that after leaving Columbia University for mandatory National Guard duty, he traded books for comics, influenced by the more modest curiosity of his new peers. “My vocabulary shrank to about four words, and you can guess what they were,” the Berkshire Hathaway founder recalled. 

For Buffett, the experience solidified a fundamental lesson: “It pays to hang out with people better than you. You float upward a little bit.”

Our new series, The Braintrust, is designed to help founders and investors float upward. In each issue, we’ll ask eight exceptional entrepreneurs one pressing operational question and then share their responses with you. It’s an easy way to raise the average of the people surrounding you, virtually. Our hope is that founders can take these lessons back to their own businesses while investors will learn how great entrepreneurs think about company-building.

We’re so excited to share the contributors for The Braintrust’s inaugural season, which will span ten editions: 

• Avlok Kohli, CEO at AngelList

• Christina Cacioppo, CEO and Co-founder at Vanta

• David Hsu, Founder and CEO at Retool

• Immad Akhund, Co-founder and CEO at Mercury

• Jack Altman, CEO and Co-founder at Lattice

• Mathilde Collin, CEO and Co-founder at Front

• Pedro Franceschi, Co-founder and Co-CEO at Brex

• Trae Stephens, Executive Chairman and Co-founder at Anduril

Together, this group has founded some of the most successful tech companies of the past generation, including many you may use and love on a daily basis. Based on their most recent public valuations, this cohort has created $35 billion in enterprise value and raised $4 billion in venture funding. Even more important than these figures are the products, decisions, and mistakes they've made along the way. 

To kick off the series, we’re starting with this question: “What do you wish you’d started investing in sooner?”

It’s a topic close to our heart for a number of reasons: what it reveals about potential blind spots for first-time founders, the role of the CEO as an internal capital allocator, the differing strategies of our featured entrepreneurs, and the lessons it offers for others in the arena. In today’s piece, The Braintrust reflects on the importance of product expansion, working with lobbyists, managing burnout, telling your story to the broader market, hiring leaders, and much more.  

Tell your story

Prioritizing external communication is absolutely something that I think all founders and company builders need to be thinking about from Day 1 – even if you think you don’t need to yet. 

From the early days of our security and compliance journey at Vanta, it was pretty clear that we had uncovered something a lot of people wanted. Because of that, we were intentionally under the radar as we built, tuned, and refined with customers – all with the goal of finding product/market fit before even really going to market. 

In my career, I’ve found the easier part is building a product. The hard part is building something people want. So, we focused first and foremost on validating ideas and narrowing in on something people wanted. We started with SOC 2 automation, and we quickly realized it was a deep and valuable problem applicable to every company –  but everyone else thought SOC 2 was this tiny, niche back office process about which only big companies cared. We purposefully stayed quiet as we built product and distribution so we could get as far ahead as possible because we knew once the secret was out, copycats would come.

And in many ways it worked – we got to $10 million in ARR before taking a Series A and had over 600 customers before we even had a real website. 

On the other hand, for those outside of Vanta, our under the radar approach gave the impression we were smaller or less ambitious than we really were. In a sense, we were too quiet: I thought that if we put our heads down and did good work, positive word of mouth would follow. And it did, somewhat, but I also let a vacuum develop that the copycats eagerly filled with their own half-truths and misstatements. The reality is that we always were, and continue to be, much larger than any of the inevitable copycats. But that didn’t always line up with how much, or little, people were hearing about us. 

When I look back, customers and the market should have heard from us more. I didn’t appreciate how important external communication can be, especially with media, investors, and analysts. At the time, if I was meeting with an investor for a speculative round years in the future, I wasn’t helping close a candidate we were excited about today, and that seemed like the wrong tradeoff. Surely, I thought, the market would see our product improvements and understand our leadership position without my tweetstorms? Some customers did, but many were busy building their own businesses. Looking back, I found it too easy to assume that outsiders would understand our vision and results because we understood them internally. The last couple of years have taught me that communicating directly is often “important and not urgent,” and it really matters.

Connect with Capitol Hill

For a company working in the defense technology space, it is incredibly important to build your government relations engine much earlier than most people might think. We learned this the hard way at Palantir. So, at Anduril, we hired a lobbyist during our first week and had our first meetings on Capitol Hill on day four. Relationships we started building during that first week are still critical to the company today.

As crazy as it sounds, it’s really important to start getting reps on this stuff early, so by the time you have a request to make, you’ve already built the key relationships. This is your responsibility as a founder. The decision-makers need to have a relationship with you, not a former senior government official you’ve brought on as an advisor. You don’t like taking time away from building your company to walk around Capitol Hill office buildings? Too bad. You either suck it up and do it, or your company dies. Your choice. Don’t hate the player, hate the game.

When it comes to choosing a lobbyist, you want someone who is culturally more similar to you than your legacy competitors. They should understand how startups work, value compensation on the upside, and know “the game” inside and out. There aren’t a ton of lobbying firms that are good at this. Hit me up if you want the names.

In the past few years, there’s been more of an awareness among lobbying firms about how they should be engaging with a tech company. Broadly speaking, though, I don’t think the function has really changed that much. The world continues to get more and more complicated, and there’s no way that a member of Congress and their staff can plausibly know everything they need to know about every bill they need to make a decision on. Someone has to guide them. 

Beyond their work on Capitol Hill, our government relations function is a critical counterpart to the product and growth teams. On the product side of things, they are surfacing areas of investment from the government that we should be building in. On the business development and growth side, they are unsticking roadblocks to acquisition and deployment. This is core to the flow of any business working closely with the government. 

Without the government relations function, you would basically just be relying on a "field of dreams" product-led growth strategy, which demonstrably doesn’t work in this sector. Keep in mind that the user of the technology is not the buyer of the technology in this space! Business development sells to the user, and government relations sells to the buyer.

Build systems to polish your product

If I could go back in time, I would have Brex focus on systematic quality and polish in our product earlier. This is not to say we haven’t aimed to produce high-quality products in the past – we’ve spent considerable time building our architecture and infrastructure in the right way to power our products. However, we didn’t think as critically about the systems and processes to ensure our products remain high quality over time. Without these systems, you’re susceptible to hiccups. We might have an amazing product now, but if there isn’t continuous rigor around how we ship updates to that product and how we track performance as more users get added, it can quickly become a not-so-amazing product. 

We have gotten much better at this over the last year, and it continues to be a huge priority of mine. For example, we’ve implemented a company-wide “dogfooding” program where we ask every employee to put themselves in the shoes of our users. Having them report on friction points puts quality top of mind for everyone at Brex. I personally have appreciated seeing all the different perspectives on how we could improve our products, and I am committed to continuing to build a culture at Brex where we break tradeoffs between speed and quality. Our goal is to build something that our customers love now and in the future, as they grow with us. 

Accordingly, I would tell my old self that it’s better to focus on doing a few things exceptionally well vs. trying to do it all. Especially in the early days, founders are strapped for resources. Focus and prioritization are key to building a product that you can be proud of and a customer experience that delivers on expectations. 

So, to summarize, here’s some tactical advice to founders who are just getting started based on my learnings: 

• Establish a framework for how to prioritize initiatives based on anticipated impact – what is really going to move the needle for your customers? 

• Focus your team on those priorities. 

• Track the right metrics of success against those priorities. Hint: it isn’t just about acquiring new users. It’s also about your current customers and the expectations they’ve developed around your product and how it fulfilled their needs.

• Then, create a strong customer feedback loop as you ship and iterate. In the early days, you spend a lot of time talking to customers. As you scale, you need to institutionalize processes that keep the customer a part of your decisioning. 

• Develop a repeatable process for communicating product iterations to your customers so they understand what it means for them and their workflows.

Invest in infrastructure and find leaders

Two areas: better infrastructure and better leaders. 

Retool has a culture of shipping quickly (for example, over the past year, we’ve launched five product lines). That high cadence of shipping was important from day one of the company (where we hired slowly despite having a *ton* of surface area). But when we were small, oftentimes we over-optimized for shipping fast in the short-term, and underinvested in stable infrastructure. At the beginning of a startup, biasing towards shipping velocity at the expense of infrastructure is the right decision (since most startups overinvest in infrastructure without even proving that they have product/market fit). But as Retool grew, we should’ve invested in better, stable infrastructure earlier, since it eventually became the main limiting factor to how fast we could ship. Investing more, earlier, would’ve been less painful. (But again, investing too early would’ve been a mistake.)

Separately, find leaders, since they are what allow your company to scale. (In a way, great leaders are like infrastructure for your company.)

Ali Rowghani has this idea that your product is your "first product", but your "second product" is building a company around the initial product such that you can scale your original product (and bring it to more people). As soon as you've proven out product/market fit with your initial product, your next job is building the company around it all. While you should build the initial stages yourself (so you know how it's done), you need to bring on the right leadership team at every stage of company growth. 

What your company needs at every stage is different. In our case, at the early stages, we needed dynamic, smart, and driven leaders (which is who we hired). That's because Retool is different from many other companies: in how we build product, in terms of how we talk about our product, and in terms of how we approach sales. The high-potential (and less functional experience) leaders we brought in were great for figuring out these kinds of Retool-specific problems.

But as the company scaled, we needed to pivot our leadership profile. Scaling from tens to hundreds of salespeople is less of a creative, first-principles-reasoning-based problem; it's a problem where the experience of having done it before really helps. I wish we had brought on experienced leaders (who had done the job at a similar scale, even if in a slightly different context) earlier; that would've saved us time. (Just like with infrastructure, it is possible to hire these kinds of leaders too early, so do be aware of hiring the right leaders for the right context.)

Expand your product early and often

Generally speaking, looking back on my journey so far with Lattice, I wish I had made each new product expansion earlier. Everything to do with the launch of a new product takes longer than you think: Building the product, the product maturation that comes with early customer feedback, and the compounding market adoption. 

Our HR Information System (HRIS) is a prime example of how long this process can take. From start to finish, it was nearly two years from the moment of deciding to start the build, hiring the necessary leaders, scoping out the build path, doing the technical overhaul, hiring up to the teams, navigating all sorts of complex organizational dynamics, and a heavy set of features...it takes an enormous amount of work and coordination. 

So, my advice to other founders would be: when you find yourself with high conviction that your product suite needs to go somewhere new, push yourself to start laying tracks in that direction as early as you can manage.

As an example of how new products that meet the strategic needs of your customers can bring big benefits to the business: When we launched our Engagement and Grow products at Lattice, the business massively inflected each time. It created a truly better experience for customers because they got a more seamless experience within the product, better data integration, fewer vendors to manage, and cheaper all-in pricing. And it was a huge boost for Lattice because we got more leads, higher win rates, more revenue per customer, and better overall retention. But each of these products was spaced two years apart – and so those benefits were, too. Looking back, it would have been possible to push them into the market faster and shrink that gap. 

So, when you know the direction your product needs to expand, push to expand early and often!