How wearing many hats can be a founder superpower
Here’s the journey I went on as a founder and what I learned at each stage.
Nelson Chu
span>span]:whitespace-nowrap”>
Most founder advice tells you to delegate fast and focus on your strengths. After six years of building Percent,
a private credit marketplace, from $80,000 in credit card debt to a
Series B, I believe the opposite: The founders who win are the ones who
do wear every hat as they go through their journey.
I’m
not advocating for micromanagement or control issues. I’m talking about
building irreplaceable domain knowledge by trying each job before you
hand it off. This framework isn’t comfortable, but it’s the difference
between founders who flounder and the ones who build the companies that
last. Here’s the journey I took and what it taught me:
Phase I: The ‘Everything Burns’ Phase (Years 1-2)
In
2018-2019, I was simultaneously acting as a customer success
representative, quality assurance (QA) tester, content creator, and
budget manager. My calendar was chaos: customer calls at 5 p.m.,
debugging the platform at 11 p.m., pitching investors at 8 a.m.
Most
people see this as unsustainable. They’re right. What they miss is that
doing customer success myself revealed which 10% of our features
actually drove retention. Managing contractors taught me exactly what
excellence looked like in each function.
So
what’s the hidden benefit behind all this? Pattern recognition. When
you’re immersed in customer service, budgeting, and product development
all at once, you start to see how each function influences the others.
For
example, during our launch, I spoke with every early customer to
understand what they actually needed. Those conversations made it clear
that our one-month investment product wasn’t just a convenience—it was a
differentiator. That insight shaped our product roadmap, marketing
messaging, and even our pitch to investors. You only uncover those
kinds of connections when you’ve lived inside every corner of the
business.
You’ll know you’re ready to evolve when you’re spending
more than 60% of your time on repetitive tasks instead of strategic
thinking. The business needs systems, not your personal heroics.
Phase II: The ‘Building the Machine’ Phase (Years 3-4)
By 2020, we shifted from doing to scaling. I focused heavily on hiring,
product management, QA, and investor sourcing. This is the hardest
transition for most founders because it requires accepting a painful
truth: your team will make mistakes you could have avoided.
Those
“mistakes” turn out to bring fresh perspective, leading to new features,
not bugs. Our first product manager found solutions I never would have
considered because I was too married to our original vision. They
questioned assumptions I didn’t even know I had.
The mental shift
here is critical. You’re no longer the best operator in every function.
You’re the architect of systems that enable others to excel. You’ll know
you’re succeeding when your direct reports can articulate your vision
better than you can.
Phase III: The ‘Strategic Leadership’ Phase (Years 5-6)
By 2022, my focus narrowed dramatically: board management, hiring, and team culture. That’s it.
This
felt wrong at first. Shouldn’t I be more involved in product? What
about strategy? Here’s the insight: everything is downstream from having
the right people with the right alignment. When you nail these two
things, everything else follows.
During this phase, I knew less
about our daily operations than ever before, yet made better strategic
decisions. Why? Because I wasn’t drowning in tactics. Our efficiency
metrics hit all-time highs precisely when my operational involvement was
at its lowest.
The
counterintuitive truth: The less you do, the more you see. When you’re
not fighting fires, you can spot the patterns that predict where fires
will start.
You’re ready for this phase when strategic decisions
matter more than operational excellence. It’s about choosing the right
mountain rather than climbing faster. You’re focusing on the things that
nobody else in the company can do and you’re not doing any of the
things that someone can do and arguably do better than you.
Phase IV: The ‘Return’ Phase (Year 7+)
Companies
have to reinvent themselves over time and this year, I’m adding back
product management, lead sourcing, and customer success to my daily
to-dos. This isn’t regression; it’s evolution.
Businesses
mature, and when they do, they need to figure out what their next
iteration is going to be. The current product is mature, and the next
act is what separates good companies from becoming great ones. In Phase
I, I was doing customer success calls. In Phase IV, I’m doing it all
over again for a very different product and a very different pitch.
Still, every hat I wore in those early days now informs strategic
decisions with 10 times the impact, with the experience and knowledge
that come with years of honing that craft.
Only founders who’ve
been through all phases have this advantage. Your competitors who hired
VPs from day one might move faster initially, but they’ll never have
your intuitive understanding of how all of the dots connect.
The
goal isn’t to wear all hats forever. It’s to wear them long enough to
understand which ones actually matter. In a world where everyone’s
rushing to delegate, the founders who do everything first have a major
advantage because they know their business at the cellular level.
ABOUT THE AUTHOR
(2)
