By Mark Weber
I've had the unique opportunity to be deeply involved in 19 different startups. I think that may qualify me as a “serial entrepreneur,” though I’m not sure that’s always a good thing.
From clean technology, the airline industry, data security, telecommunications, LCD hardware, software, two de novo banks, mortgage franchising, payment systems; fintech and a marketing agency, I helped raise millions of dollars funding them.
I often led marketing strategy and branding along the way. I learned so much; unfortunately often the hard way. One day I’m gonna build my “stock option shame” framed wall of failed startups. Thankfully, I’ve also had some wins.
Each startup was unique, offering its own set of challenges and rewards. They all began with unbridled optimism, a belief every risk and hurdle could be overcome.
When I first launched my own marketing agency decades ago, I was exiting a large bank merger and trying to decide whether to find the next company to work for or take the plunge of my own startup. I wrote this note to myself at a Ritz Carlton hotel I was staying in that I still keep near my desk: “The security of corporate life and a steady paycheck no longer outweigh the risks and rewards of entrepreneurialism.”
I took the plunge, but not just once.
Along my 19 startup journeys, I've picked up some invaluable lessons I thought I’d share:
Most Entrepreneurs Fly on the Trapeze Without a Net
The journey of launching a scalable, high-reward startup requires some sense of invincibility from failing. You believe there’s no turning back - and fight to convince everyone around you the same. It's fraught with early thrills and optimism that turns into rising hurdles, unexpected turns, and inevitably some hot messes; even failures. No net below to catch you.
I’ve learned that inside that entrepreneurial driving tension is an opportunity to keep your hubris in check - and seek out mentors. Humbly gain wisdom you can never build alone in a lifetime (OK, unless you are Jeff Bezos or Elon Musk - kudos to you both if you’re reading this). That’s a safety net to balance taking risks and picking which battles to fight to win another day, or another way.
Failing is Sometimes More Rewarding than Quick Victories
It was always easy for me to get caught up in the thrill of early successes: landing investors, turning beta tests into real products, cutting deals, growing revenue. But it's been the failures that brought my most potent lessons. They gave me insights into my own character and reshaped my values into what matters most. Failure can either foster resilience and learning lessons, or churn into self-doubt.
I’ve let the burns teach me something new each time I could use later. Take time to keep re-assessing what will be a series of moving targets, and learn to adapt quickly. Celebrate what you learn in your failures and use it to grow, instead of grasping for quick fixes that are not your disciplined strategic advantages.
Taking Risks Sounds Simple Enough. It Isn’t.
Each startup risk brings with it risks and the great possibility of failure. The chance of losing money for the people and friends who bet on you is a driving motivator; just as creating opportunities, new jobs and careers for people who count on you for a successful outcome.
That immense personal pressure you feel to perform is the price of chasing startup success. Taking risk initially to launch a startup is pure adrenaline. Sustaining a startup through its dynamic phases, rises and falls takes mental stamina, laser focus and the ability to listen well, and adapt to changes around you. It is not a time to ignore warning signs, or explain away rising risks.
It also requires a balance of driving conviction, keeping people focused on (and celebrating) the small wins, not the setbacks that arise. And regularly measuring and updating strategic plan scenario options, and emerging risks against real outcomes so you can adapt.
Hiring the Smartest Team to Win is a Fallacy
Don’t get me wrong, hiring great talent, experience and intelligence is great, but it's not everything.
When building a team, I’ve learned it's critical to look beyond the IQ and experience, and into the EQ of individuals whose character will shape the overall culture, teamwork and honest feedback you need to persevere in tough times.
I prize personal values that align with ours: profound curiosity, determination, failures learned from, empathy for others, and people who listen, and can adapt. These traits are essential to building a High Performing Team.
I’ve learned to listen actively, weigh the cultural fit, sniff out a deep work ethic, prize adaptivity and passion that every potential hire brings to the table.
I’ve used these lessons, especially listening to my team, to help shape some of the guiding principles and purpose at two of my startups, Strum Agency and, most recently, Strum Platform.
We help credit unions, fintechs and community banks nationwide tackle their most challenging strategic growth opportunities and competitive market and brand positioning to stand apart and win.
We leverage our past learnings, tech stack and data insights to uncover and create the growth strategies, data-driven marketing processes, emotive brands, and purpose-driven cultural focus that aligns people together to keep hitting the right chord together at the right time. Orchestration is amazing when it works well; game changing shared understanding with people clear on their purpose and collaborating to achieve results.
The Hard Lessons Learned
In my journey of being a serial entrepreneur, I’ve learned it's not just about the destination, the wins, or declaring victory. It’s also about the hard lessons we learn; the people and relationships we build and learn from; the challenges we overcome together; and the growth we experience in our companies and inside ourselves - especially in failure.
Mark Weber is CEO of Strum Platform, Seattle.