The Founders Guide to Mastering New Parts of Your Business
In this edition of The Braintrust, eight unicorn founders share the strategies they use to master new parts of their business.
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One of the most profound realizations of adulthood is that you, alone, are responsible for your education. Once you have left the halls of high school, college, or a graduate program, suddenly (and usually irrevocably), the burden of learning rests firmly on your shoulders. No longer will seasoned teachers direct you toward useful books, ask your thoughts, and test your comprehension. Gone are the days of being served a steady curriculum to follow and master.
Work hopefully provides some education, but its pedagogy is often lean, narrow, and ruthlessly practical. Time and experience often make it worse – the better you become at a singular valuable task, the more your employer will likely ask you to focus on it, which might not feed your curiosity.
Generalist readers recognize this reality and understand the competitive advantages this dynamic affords. If adulthood is a time when many slow their learning rate, those who accelerate can see outsized benefits. These learners fight against the incentives and distractions of the grown-up world and read good books, subscribe to intelligent publications, meet interesting people, and generally keep pushing the boundaries of their understanding. Though the results of such efforts are not always tangible in the short term, they tend to be invaluable in the long run. It is no coincidence that many of the world’s most successful people are also among the best read.
Because of the nature of this readership, I think you’ll especially enjoy today’s piece. It asks eight world-class founders to share their techniques and strategies to level up and learn new areas of their business. In the professional world, few vocations require as much rapid education as a startup founder, a role that requires flexible intelligence and constant adaptation. On any given week, a CEO of an early-stage company might split their time between decoding governmental regulations, hiring staff, wooing investors, parsing deal documents, reviewing code, weighing in on design, running a marketing campaign, and making sales. It is a learning treadmill that doesn’t stop. Though some functions are absorbed as a business grows, an innovative company will always find a new frontier to conquer.
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In brief
If you only have a few minutes to spare, here are eight highlights from The Braintrust’s contributors on how to supercharge your learning.
Mathilde Collin trades thoughts with similar-stage CEOs in a private WhatsApp.
Christina Cacioppo reminds herself of Ira Glass’s advice on the gulf between taste and quality.
Pedro Franceschi read deeply and leaned on his leadership team to guide Brex’s SaaS push.
Jack Altman believes in learning by doing – experience often trumps a textbook.
Immad Akhund learns by listening to experts and using their knowledge to inform decisions.
David Hsu relies on first principles thinking – except for well-trodden problems.
Trae Stephens believes founders can’t be Superman; they must assemble a team of X-Men.
Avlok Kohli guided AngelList through the SVB collapse by absorbing information rapidly.
“I have a WhatsApp group with four other SaaS CEOs”
Mathilde Collin, CEO and Co-founder at Front
This is the single most important thing you need to do as a CEO: learn faster than the pace at which your company is growing. It’s hard. Here are six things that have worked for me:
It starts with telling yourself and others that you don’t know something. To be able to admit this, you need to have enough self-confidence and enough self-awareness. Having a coach or a therapist (or most likely both!) will help. Surrounding yourself with people who believe in you and will help with your self-confidence is key.
Read! Some of my favorite books are The Effective Executive, High Output Management, and The Hard Things About Hard Things. First Round Capital also publishes good content.
Create a group of peers (similar-stage companies) you can learn from. I have a WhatsApp group with four other SaaS CEOs of Series C-E companies.
Ask CEOs/leaders who are ahead of you: every CEO/leader is asked to reinvent the wheel on topics that have been thought about before by hundreds of smart people (how to run all hands, how to scale comp, how to performance manage, how to design goal setting, etc.) I’ve tried to write about many of these things, but I also never hesitate to ask leaders of companies that I think are well-run.
Ultimately, you’ll need to hire people better than you for areas where you have less experience. That’s how you’re going to keep learning. Before hiring for a new role, ask people around you who they consider the top 1% for a certain role and meet with those people to calibrate. (Bonus: they might end up joining your company!)
Do the work! The best way to learn about sales is to sell; the best way to learn how to tell stories is to tell stories. By doing the work, you’ll also be able to know what to look for when hiring for these roles or skills.
“I distinctly remember running in Golden Gate Park one morning and realizing, ‘Oh, I feel like I'm bad at everything, because I am.’
Christina Cacioppo, CEO and Co-founder at Vanta
As a product person, I like learning new things – it’s usually fun for me. But I’d be lying if I said it wasn’t harder to find that joy when the stakes were higher as a first-time founder and CEO at Vanta. Folks who joined Vanta were relying on me!
Years ago, I read this snippet of advice from Ira Glass, the host and executive producer of NPR’s This American Life. It’s a bit long, but I still think about it often:
We get into it because we have good taste. But it’s like there is this gap. For the first couple years that you’re making stuff, what you’re making isn’t so good. It’s not that great. It’s trying to be good, it has ambition to be good, but it’s not that good.
But your taste, the thing that got you into the game, is still killer. And your taste is good enough that you can tell that what you’re making is kind of a disappointment to you. A lot of people never get past that phase. They quit.
And if you are just starting out or if you are still in this phase, you gotta know it's normal and the most important thing you can do is do a lot of work. Do a huge volume of work. Put yourself on a deadline…It is only by going through a volume of work that you’re going to catch up and close that gap. And the work you’re making will be as good as your ambitions.
It takes a while. It’s gonna take you a while. It’s normal to take a while. You just have to fight your way through that.
Once we had the skeleton of a first product, I started doing everything else besides product development: recruiting engineers, sales, outbound emails, putting together a budget at an investor’s request, etc. “Everything else” was new to me – I hadn’t done any of it, and I generally felt like I was bad at it all. I probably was bad at it all! I was learning on the job.
And as Ira Glass says, in the beginning, literally nothing meets your taste bar. I distinctly remember running in Golden Gate Park one morning and realizing, “Oh, I feel like I'm bad at everything, because I am. Because I’m learning. But my job at this stage is to do things well enough to convince someone who’s actually good at them to work at Vanta.”
When you’re learning something, it’s uncomfortable. You won’t feel like you have mastery over what you’re doing, but that’s the point – if you’re only doing things you have mastery over, you aren’t doing your job as a founder.
I constantly remind myself that my job is to get up to speed, to be just good enough that I can convince someone who is very good to join Vanta. I’ve also found that by fighting my way through and focusing on getting to “good enough to bring in experts,” I’ve ended up mastering much more than I thought I would.
“There’s nothing better than an ‘aha’ moment”
Pedro Franceschi, Co-founder and Co-CEO at Brex
Henrique and I constantly have to learn new areas of the business. In the past year, much of that learning has been regarding SaaS go-to-market processes. Still, every year, there’s a new area of the business we need to dig deeper into and understand better to make the right strategic decisions for the business. There’s no silver bullet to this, so we have a number of different avenues for learning.
The first is reading. When there’s an area of the business we want to understand more, we’ll read multiple books by experts in that field. This helps us create an overarching understanding of the topic and learn how other leaders have addressed issues Brex may be facing.
The second is listening, and we make it a priority to talk to other CEOs and subject matter experts. These conversations are especially helpful in thinking about the building blocks of whatever area of the business we’re trying to improve. We may know what the ideal end state looks like, but live conversations about breaking down where to start and how to progress are hugely helpful in moving toward that end state.
A key piece of this learning is involving our leadership team. Sometimes, we’re learning about a new area of the business so that we have the right context to make a key leadership team hire. Other times, we’re just diving deeper into a specific area of the business, and we have a leader in place who is a subject matter expert. As we read up on the subject, our leadership team is often who we’ll go to first with questions. If we want more outside perspectives, they’ll be on those calls to ensure we’re getting as much out of them as possible.
While understanding new areas of the business can be intimidating, it’s ultimately also incredibly rewarding. I am a builder at heart – that means I want to take things apart and figure out how to put them back together, and I am naturally curious about how things work. This has always driven me, and it is this mindset that helps me navigate new areas of the business. There’s nothing better than an “aha” moment when you have a breakthrough, when you look up and realize you get it, you’ve figured XYZ out.
“Just jump in the pool and figure it out”
Jack Altman, Co-founder and Executive Chairman at Lattice
I’ve found that the primary source of learning for founders is experiential learning – especially when it’s an area where you have no previous expertise. Instead of getting a swimming lesson, you just jump in the pool and figure it out. Instead of taking wilderness training classes, you’re just left in a forest – and you have to figure it out.
The bad news about this kind of learning is that it’s really, really hard. I can’t underscore this enough. But the good news is you learn much faster and develop a deeper understanding than people sitting through metaphorical courses. As the cavalry comes in and you build out your team and get a bit more of a product-market fit, you will get to learn from experts in multiple fields. Ultimately, as a company grows, you get to hire people with tons of specialized experience across engineering, marketing, finance, legal, and sales – and I’ve found you can learn so much from them as a founder.
One final note on this: One thing I appreciate about Silicon Valley is how supportive it is to founders. There is so much infrastructure and content out there for founders to learn about building companies from peers and mentors, and this can be enormously helpful, too.
“If I’m figuring out a complicated subject, I might talk to 10 experts”
Immad Akhund, CEO and Co-founder at Mercury
Step one of learning for me is figuring out what I actually need to learn about or what my company’s biggest problems and pain points are. Answering that question comes down mostly to a combination of three things:
What’s going on with the company or the current stage of your business;
Talking to slightly more scaled-up entrepreneurs, either casually or in group settings;
Talking to investors who have experienced bigger companies who can help point out things you might be missing.
Once you know what your biggest problems are, that's when you can say, “Okay, I really need to learn how to do this thing.” At that point, it’s about how you learn to do it. For me, I learn a lot by talking to people. Occasionally, I might learn from books or something like that, but my main course is always to try to talk to a bunch of experts in that field. So, if you’re trying to tackle your company’s finances, for example, I would go out and talk to a bunch of CFOs.
I’ll typically tailor the approach or number of conversations to the subject. For example, if I’m figuring out a complicated subject, I might talk to 10 experts, whereas a simpler subject or something that feels a little more intuitive might just call for two or three conversations. And for something a bit more straightforward and tactical, like implementing OKRs, that’s when I might just look for a good book or blog post to help me learn about the thing quickly. (In that case, when my team and I decided we needed an OKR system to set better goals internally, I found Radical Focus by Christina Wodtke to be a helpful read.)
I think the main trick to learning well as a founder is to treat every resource – conversations, books, blog posts, etc. – as one single data point that will then inform your own strategy or approach. Basically, you shouldn’t think about learning as simply absorbing information and then mimicking what others are doing, but actually understanding how and why they’re doing what they do and then melding that to what makes sense for your company. Think about your stage, industry, size, culture – any factors that make your company unique. That’s when you’ll be most effective.
“I’d bet that Jony Ive at Apple has thought more about how to structure a design team than you have”
David Hsu, Founder and CEO at Retool
First principles thinking gets you pretty far in many areas of business. For example, thinking about your business model, your value proposition, and how you price can all be done from first principles. If you’re trying to decide on a pricing model, you might ask how or why customers derive value from your product and in what cases they’ll derive more or less value (e.g. a number of transactions, a number of users on your platform, etc.). Then, you can try and understand their willingness to pay and figure out how much value you want to capture. Pretty simple.
When thinking through these problems in a first-principles way, understanding the space of all possibilities is often helpful in deciding what is right for you. For example, in the pricing example above, you might study other SaaS companies and understand why, in some cases, the pricing is metered (e.g., based on the # of transactions) vs. seat-based. You can also test yourself by attempting to explain why other companies would make the decisions they’ve made.