Stew Bradley

After 5 years of doing this job, certain lessons stand out—things I thought were important that ended up being wrong or unimportant, as well as new realizations that have fundamentally shaped how I approach venture investing. This is a scattered collection of learnings, reflecting the breadth and variation inherent in our daily work. Venture investing, at least the way we practice it, requires constant context switching. Sometimes the challenges a founder faces are personal, sometimes they are strategic and long-term, other times they are purely tactical. Hopefully this collection of thoughts reflects that varying nature.

The goal here is not to paint a utopian view of venture or running our own firm, but to describe some of our learnings, highlight the value of the mundane day-to-day work, and convey it clearly and without varnish. This will be a living document that I periodically add to, as new insights and lessons emerge from my ongoing journey as a seed-stage investor.

1 - Aptitude and Adaptability Are Not Correlated One of the key lessons I've had to grapple with over the years is that aptitude and adaptability are not inherently correlated. Just because someone demonstrates a natural talent or proclivity for a certain skill set doesn't mean they'll be able to seamlessly adapt to new challenges or changing circumstances.

I can recall several instances where we backed founders who were undeniably brilliant—technical wizards or product visionaries. On paper, they had all the right ingredients to build a successful company. But when faced with the messy realities of scaling a business, navigating complex organizational dynamics, or pivoting their strategy, they often struggled. Their aptitude in one area didn't automatically translate to the adaptability required to lead through uncertainty and change.

Conversely, I've seen founders with more modest individual capabilities absolutely thrive by virtue of their ability to learn quickly, solicit feedback, and evolve their approach. They may not have been the most naturally gifted, but their willingness to adapt, iterate, and grow with the business made all the difference.

This realization has been a humbling one, forcing us to rethink how we evaluate and support founders. It's no longer enough to simply identify raw talent - we have to dig deeper, assessing not just what someone can do, but how they'll respond when the ground starts shifting beneath their feet. Adaptability, resilience, and a growth mindset are often better predictors of long-term success than pure aptitude alone.

Of course, the ideal is to find founders who possess both—the natural gifts and the adaptive capacity. But when forced to choose, we've learned that the latter is the more reliable indicator of a company's ability to navigate the inevitable ups and downs of the startup journey.

2 - The Importance of Self-Awareness One of the most important, yet often overlooked qualities we've come to value in founders is self-awareness. The job of a founder is constantly evolving, especially in the early days of a company's life cycle. What may have been a founder's core expertise in one iteration of their role often doesn't carry over seamlessly as the responsibilities shift and change.

Sometimes these role changes happen quickly, like when a new hire joins and takes certain tasks off the founder's plate. But more often, the transformation is more gradual as the company matures and scales. In these cases, a founder's ability to critically assess their own performance, identify where they're struggling, and recognize where they need to improve or seek help is invaluable.

The same holds true for us as investors. Our roles and the demands on our time are in a state of perpetual flux, which can make it challenging to always exhibit the same level of self-awareness that we look for in founders. It's easy to get stuck in our ways or fail to adapt our approach as the needs of the market and our portfolio companies evolve. And that lack of self-reflection can undermine our effectiveness as partners and advisors.

However, the best founders and investors we work with make a concerted effort to take an honest look at their own strengths, weaknesses, and areas for growth. They're proactive about seeking feedback and aren't afraid to ask for help when needed. This self-awareness allows them to stay agile, continue learning and improving, and ultimately deliver better outcomes for their companies and investors.

It's a lesson we're always working on - that personal development and growth, for both founders and investors, starts with self-awareness. Staying in touch with our own skills and blind spots is crucial to providing the most valuable support to the entrepreneurs we partner with. It's an ongoing process, but one that has undoubtedly shaped how we approach our work and our own continuous improvement.

3 - Tailwinds are underrated It's widely understood that strong market tailwinds can provide a significant advantage for businesses. The basic premise is simple—the stronger the tailwind, the more runway a company has to experiment, iterate, and course-correct.

However, what's been surprising in our experience is just how dramatic the delta can be for startups operating in markets with powerful tailwinds versus those without. This is particularly important at the seed stage, where so many variables are at play and the margin for error is smaller. It's not just a marginal difference, but a chasm that can make or break a company's chances of success.

Founders building in markets with weak or nonexistent tailwinds are essentially operating in "startup hard mode." They have to work exponentially harder to overcome inherent headwinds, whether it's educating the market, driving adoption, or fending off entrenched competitors. The probability of success is simply much lower.

Conversely, startups riding the wave of a strong market tailwind often achieve scale and success far more quickly and with less friction. Customers are more receptive, capital is more readily available, and the overall environment is more forgiving of missteps. It's not a free pass, but it does provide a crucial buffer that can make all the difference.

Of course, this doesn't mean we’re focused on investing in "hot" sectors. Part of our job is to identify emerging trends and opportunities before they become obvious. But it does underscore the importance of thoroughly understanding the market dynamics and competitive landscape before diving in. It's a lesson that has shaped how we approach our diligence, our portfolio construction, and our ongoing support of founders. We know that even the best teams and ideas can falter without the wind at their backs.

4 - Venture is about the problems It's easy for founders to get caught up in the excitement of building their solution. But the most successful ventures are those that truly understand the nuance and complexity of the problem they're solving. Too often, founders are so enamored with their product or technology that they don't spend enough time deeply investigating the problem space.

What are the root causes? Who experiences the pain points, and how severe are they? What are the existing approaches, and why are they falling short? Founders who can demonstrate a nuanced, data-driven understanding of the problem are the ones most likely to build enduring, impactful businesses. To help founders to go beyond the obvious symptoms and really interrogate the problem from all angles, we put together our Research Hub to serve as a guide during problem discovery.

5 - Living with tradeoffs Balancing tension is at the heart of good company building. It's all about tradeoffs—startups are not static, ordered machines, but rather vital living organisms that are never perfect. The beauty of this is that they can be adjusted and re-architected as needed. But doing so is hard work. There are no easy answers, no perfect solutions - just a constant process of weighing options, making tough calls, and adapting on the fly. Uncertainty comes with the territory, and getting comfortable in the gray zones is often difficult for founders. This is where investors can provide a steady hand, helping founders find their footing. Guiding founders through these choppy waters is one of the most rewarding aspects of the job.

In the face of uncertainty, we've found that helping founders focus on the inputs—the things they can control—can empower them to navigate the ambiguity. By shifting their attention to the daily actions, processes, and decisions within their sphere of influence, founders can find a sense of balance and stability when the path forward is unclear.

6 - High context is the best way to stack odds Productive support to founders in the early days requires context—an up-to-date view of what is happening in each startup. Not just the highlights that might go into investor updates, but an unvarnished view of the moving pieces. This is a perspective that is only shared when the founder trusts us, and is something that we have to earn.

We've found that the best way to build trust and maintain high context is through consistent engagement. Adding value early and often is key. A common way this manifests is by assisting founders with important but routine challenges. We can't cherry pick the issues that are “worth our time.” If you want the unfiltered feed from a founder you have to be ready to eat it all. This approach requires more time, but enables us to better understand each business, anticipate needs, and deliver more impactful support to our portfolio companies.

7 - Good internal systems help manage the context switching Working with dozens of companies requires constant context switching. You need a solid internal system to stay on top of what's happening and avoid context collapse.

At our fund, we use a centralized workspace to track interactions, decisions, and action items. We meticulously log details in this system, allowing us to easily reference the full context of a given situation and see a clear snapshot of our thinking at that time. The linked data also helps us monitor key metrics and hold founders accountable—if it gets measured it gets managed. Maintaining this system takes time, but it makes managing the multitude of workstreams much easier. In fact, as our connected system has grown, we've been able to identify serendipitous opportunities—we now regularly connect people with related "asks" that we've collected over time.

The key is that we have a set of internal best practices that we stick to, and consistency in how we use the tools is more important than the specific tools themselves. We collect company details for all our interactions, though the information can be spotty outside our portfolio. This still provides value by informing how we support founders. The system's value has only increased over time.

8 - Consistency is what separates a good coach from a bad one Consistency is a huge factor in effective coaching and advising, and it's important on multiple vectors. There's consistency with the standard of excellence that you hold founders to. Consistency in your preparation when serving a founder. Consistency in not letting stress from other areas impact how you interact with a founder. And consistency in your energy and dedication to the work.

My experience in the NFL really hammered this lesson home. The best coaches I worked with established a standard early and stuck to it. The outputs didn't change how they viewed the inputs. Meaning if we won a game, but I had poor technique on a certain play, that would still be addressed.

Feedback loops can be long for founders, but their interactions with investors shouldn't be one of those. The inputs and outputs need to align—how you show up needs to be consistent. If you're having a shitty day, you can't bring that baggage onto a founder call. Like inputs should produce like outputs, every time.

This level of consistency is what separates the good coaches and advisors from the bad ones. It builds trust, credibility, and a sense of reliability that founders can depend on, even in the face of uncertainty. And it ensures that your guidance and support remains valuable, no matter what challenges the business is facing.

9 - Prove yourself wrong Investing is a craft, not a destination. There is always more to learn, skills to hone, perspectives to gain. Learning is the lifeblood of this job—but it's not just seeking out knowledge that matters, but actively looking for ways to prove yourself wrong (not justify past decisions) that is vital to long term success. Mistakes are opportunities to learn and grow.

Obsess over the little things—for investors, that might be the questions you ask in diligence, the rationale for passing on a deal, or a snapshot of your thoughts about a port co ahead of a regular catch up. Being intentional about these tasks and keeping records of your thinking creates a ton of data points that you can reflect on later to spot mistakes or things you missed. The accumulation of these mundane moments can lead to mastery or mediocrity, depending on the approach you take. Finding out you were wrong is a gift because it brings you closer to the truth. Stay humble, curious, and committed to the daily work.

10 - Knowing the difference between white gold and platinum Building a solid frame of reference for a problem space is the only way to tell good from great. And the key to developing that discernment? Reps, reps, reps.

Just like an art connoisseur who can spot authenticity and quality after seeing countless paintings, the more startups we're exposed to in a given space, the stronger our intuitive sense of what sets the great opportunities apart. It's not enough to just understand the surface-level details of an industry - developing this intuition requires time, dedication, and a relentless curiosity to dig deeper.

The more we immerse ourselves, ask follow-up questions, and look for patterns, the more prepared our minds are to recognize the platinum from the white gold. This discernment is everything in seed stage venture—it empowers us to make smarter investment decisions and provide founders with strategic guidance that goes beyond the obvious. It also provides motivation to approach all of our interactions earnestly because each new startup, industry, and founder interaction is an opportunity to sharpen our perspective.

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Reflecting on the past five years, I'm humbled by how much I got wrong or didn't see clearly. I know that if I look back on today five years from now, I'll likely feel the same sense of growth and humility. But I hope that with each passing year, the misteps will be fewer and farther between.

What hasn't changed is the joy this job brings me. The evolving challenges, brilliant founders, and deepening partnerships continue to motivate and inspire me daily.

I'm excited to keep learning and growing alongside the incredible teams we support. Here's to the next five years and all the lessons yet to come!