I Disagreed With a Top VC—and It Made Me a Better Founder

Patterns of Success vs Patterns of Failure

About 1.5 years ago, I was talking to one of the most well-known VCs in the Valley. We were catching up about startups given I was angel investing very actively, and I asked this individual what he looks for when making investments.

He didn’t miss a beat.

“There are no patterns of success. Only patterns of failure.”

At first, I nodded. It sounded smart. And yeah—there are a lot of ways for startups to blow up.

But after sitting with it, reflecting on the hundreds of founders I’ve worked with—and honestly, living through a lot of this myself through building out Sage —I disagree.

There are patterns of failure, for sure. But, there are definitely patterns of success too.

The #1 pattern? It’s this:

Can you learn from failure?

Can you look inward and own what went wrong? Can you change? And do you have the resilience to do that—not once, but over and over—mornings, nights, weekends, for years, when you’re exhausted?

Because if you can, it’s “when, not if” you will succeed. That’s the pattern I look for in investing in great founders. That’s the pattern I try to live myself, as an entrepreneur.

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Patterns of Failure

There are definitely patterns of failure in the 0 to 1 phase. We all know how difficult it is for an early stage startup to succeed. And, I have seen the same stuff blow startups up over and over again in the early stages:

• Mismatched cofounders. People who aren’t values-aligned. Or who bring the same strengths (and same blind spots). On day one, it looks exciting. Twelve months in, it’s chaos.

• Running out of cash. I recently met a founder doing $2.5M in revenue, growing 100%—incredible progress. They were obsessing over whether to raise a Series A or a B (e.g. a closet way to figure out how to maximize their valuation). But digging in further, I learned there was only a few months of run-way left. The real question was: how did you end up with only a few months of runway? And why are you obsessing over your valuation, when your dream is over in a few months if the markets turn? Cash buys time. Time buys learning. Without it, game over. So many startups fail because they run out of money. You are focused on the wrong thing.

• Building in a vacuum. Founders fall in love with their own ideas. They build the thing they want to see in the world. But they skip the hard part: actually talking to users. Starting with empathy. Asking questions. Understanding pain.

These are patterns. You see them again and again. But, to me, if you recognize these patterns of failure, and you have a process from learning from your failures, it is not “when, not if” you will succeed.

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Patterns of Success

The pattern of success I see in early stage start-ups are founders that are relentless learners, and can learn from their own failures, over and over and over again. The humility to look inwardly to recognize the failure, and the confidence to move forward with those learnings. Every rejection, every failure hire, every failed customer conversation, every product launch that results in zero users, is an opportunity to learn, and to grow. Failure cannot be avoided, but being able to learn from the failure, and course correct, is a pattern of success.

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Recruiting: One Hire = 1000 Failures

After we raised our round last year, and in particular given a fairly significant track record in entrepreneurship, I thought recruiting would be easy. It wasn’t. I don’t think enough people talk about how difficult it is to pull a founding team together. The people stuff has always been the most difficult for my mental health - you have to balance serving the individual vs building a team that maximizes your chance to succeed.

When recruiting is the biggest priority, I spend every morning for months —2.5 hours a day—on LinkedIn. Sourcing. Combing through my contacts and text messages. Asking for referrals. Searching. Messaging. Repeating. I did 15-minute intro calls back to back. Most people didn’t reply on Linkedin. I did not care - I’d send them a text. And if they did not respond there, I’d message them on facebook messenger. Some were curious but passed. Some folks did not want to work in healthtech. Some said they’d move to the Bay Area, then didn’t. Some found out the commute would be longer vs expectations, and then decided the opportunity was not a great fit for the family.

It’s death by a thousand cuts - it always hurts to be ghosted. It always hurts when you pour your soul into looking for people, and they do not work out for whatever reason.

To me, each of these thousand cuts is an opportunity to look inwardly. To develop a pattern of success. Think about it - if you get 1,000 rejections, and you create the inner space to ask “why”, and you examine the reasons, and you course correct, it is “when, not if” your team will come together. It’s hard to predict how long it will take. But, if you trust your process, it will come together. It’s not one magic silver bullet, and that’s not what this post is about. The pattern of building the team comes from the process of experiencing the inevitable failure, digging deep, asking why, getting those learnings, and then course correcting. That process is the pattern of success.

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Early Customers: You’re Not Pitching—You’re Balancing Listening with Pitching

Right after paternity leave, I jumped straight into customer mode. For context, Sage is a B2B company building AI-powered care navigation. Our technology enables health systems to make it easier for patients to find the right doctor, help doctors spend their time on the patients who need them most, and make sure patients get care faster. We have a lot of repeat entrepreneurs on the team - and our motivation to build this company into a legendary business comes from the desire to do good through serving others.

While I was on paternity, our tech team had made significant progress re: building an AI medical assistant to power our products. The benchmarks were out-performing the #1 model re: diagnosis and triage, and it was clear it was time to bring this technology to the real world to help people. We had deliberately chosen to build out the core technology to be robust vs adding a wrapper on top of ChatGPT. We had chosen the approach of building out the technology infrastructure prior to finding customers. It was time to sprint on go to market. In four weeks, we talked to 57+ prospective partners, multiple times a week.

Thankfully, 95% responded to our request for an initial discussion. Perhaps this was due to the success of our prior ventures, or perhaps it’s because we were hitting on an important pain point that they were experiencing. But after every call, we would ask for feedback. Some said the space was too crowded. Some said we were not focused enough. Some said our product did not address their problems. Some had trouble understanding the vision. Some were so overwhelmed they did not have any capacity to onboard any other subjects.

After the majority of the calls, I’d feel beat, wondering what we did wrong. The first thing I often did was to hit some pickleballs as hard as I could. The feedback always hurt. But rather than immediately address the feedback, and try to find solutions, I’d first clear my mind. It’s harder to solve hard problems when you are feeling frustrated and beat up within. So, I’d go hit pickleballs, clear my mind, and then re-visit the feedback in the evening.

Again, the pattern of success here is experiencing the inevitable failure, digging deep, asking why, getting those learnings, and then course correcting. And, in this case, adding a step to clear the mind to be able to see the problem more clearly, before coming up with solutions.

Turns out we were doing too much pitching, and not as much time listening. We came in with open-ended questions. We created psychological safety to figure out the pain points on the ground. And from that came clarity: burning pain points. Something our partners needed solved yesterday.

The more that we listened, the more we asked questions, the more refined our product roadmap became. The more we built features into our platform that actually solved the specific pain points of customers. The ordering of which problems to solve. The more refined our prototype and pitch decks became.

You never know how long this stage of the startup will be. To me, the things within the control of an entrepreneur are making sure your balance sheet is enough to sustain this part of the journey, ideally for 24 mo+. That’s why we raised more capital than we needed. Having more run-way gives you more time to figure things out. It gives customers more security that you are in it for the long haul. I completely disagree with VCs that give you a small check, and ask you to find signs of success in 6 months and come back for more. They are optimizing for their own returns and portfolio vs the success of the entrepreneur. Avoid these VCs unless you really need money.

The other thing within your control is to continue the outreach, listen to the feedback, get to a good mental space, and then make changes. As I reflect on this sprint, 2.5 months later, it has been painful, but it has been a phenomenal success. There are going to be multiples more engagements this year than we can support, at the current team size. So, we’ll need to look at growing the team soon, perhaps even pulling forward a growth round, which is exciting! The next big rock for the company.

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Final Thought

If there’s one pattern of success that matters more than anything else, it’s this:

The ability to learn from failure.

It’s the humility to look inward. The courage to make a change. And the resilience to do that day after day, through every hard thing this journey throws at you.

The world needs more entrepreneurs. Entrepreneurs are change-makers that help to push the boundaries of what is possible.

side note: it’s been hard to keep writing while running a company, a fund, and being a new dad. the intent in writing is always to try and help. So, if you found this helpful, please shoot me a note, i’d love to hear from you :)