Not to Lose

I’ve been around soccer the majority of my life.

Whether it was traveling with the college team my dad coached as a kid, playing club soccer at an early age, focusing on the sport in high school, playing all through college, or being the product of my first entrepreneurial venture, soccer was a part of my identity for over 20 years. This team sport helped me push to be my best, but the sense of belonging is what made it special.

As I’ve enjoyed the World Cup in Qatar, I’m reminded how easy it can be to get ahead in a match, before slipping into a dangerous trap. Instead of staying sharp by maintaining the offensive pressure that earned an early lead, it’s tempting to start playing not to lose.

In soccer, this often means a team sinks back into an overly defensive formation. Less variety invites frantic desperation and the added pressure often leads to an equalizing goal being scored by the opposing squad. Even if the need for another goal shifts your team back into a more balanced attack, the momentum has shifted.

When applied to business, getting ahead and then playing not to lose can be seen all over the map. For instance, snagging a few early adopters, then assuming customer discovery is over. Hiring new talent, then hoping everyone can work together without initiative. Launching a new product with existing customers, then not supporting them through the chasm of change. Securing product-market fit, then avoiding innovation due to a misguided sense of risk. Finding generous mentors, then forgetting to nurture relationships. Those are just a few, but many leaders are lulled into this trap that’s defined by a sense of scarcity.

Tactics to stay ahead differ based on situational factors, but when in doubt, trust that uncertainty is certain. Be strategic to avoid recklessness, then stay on the offensive by leaning into the pain. As you find fresh ways to serve customers, continue celebrating milestones and stay ahead with initiative to keep building beyond the fear of losing.

Sticks on Ice

A friend suggested I write about micro vs. macro.

These two words have related, but opposite meanings. Everything happening right now (micro) is transitory, yet these micro-moments coalesce into the story of our comprehensive progress (macro).

The distraction of each micro-moment is impossible to avoid, but the Canadian saying, keep your stick on the ice, reminds us to chill, keep it simple, and be ready for anything. No matter where stuff lands on the spectrum between good and bad, micro eventually accumulates into macro. Alright, take a deep breath, enjoy a sip, and let’s brew on how staying mindful of the macro, helps us appreciate the micro.

Extra Shot

Want me to lean into a topic on your mind? I’m ready when you are.

Last week’s writing on intrinsic motivations seemed to resonate, as it was encouraging to hear from many of you. After a few dispirited days, I was back at full speed with Global Entrepreneurship Week. Our web3dsm gathering, 1 Million Cups, an angel investor event, premiering our Techstars Iowa Accelerator 2022 Demo Day video, and watching friends like you bring so many things together, was a groovy way to celebrate entrepreneurs who serve their local communities and bolster the global economy.

A focal point for me, was an opportunity to speak at the United Fall Leadership Conference. To maximize the impact, I cranked up the volume in a new talk tuned specifically for students and educators. I call it “No Permission Required”. The energy of accelerating others is unmatched, but there’s an extra boost as we’re exploring education and making a ruckus to activate linchpins along the way! It was cool to connect with 200+ high school students from all around Iowa and one of my sessions was recorded, so here’s me sharing my heart in full effect.

Alright, by now you’re thinking, how does this have anything to do with micro vs. macro or staying ready for anything by keeping your stick on the ice?

Well, after this whirlwind of wonderful, the brutal cold season found it’s way into our home. The highs of so much stimulant collided with the lows of isolating sickness. As always, mental fitness was tested. Within the worry of caring for loved ones and the frustration of my own pain, the goodness from days before felt distant. Agitation is hard to fend off during tough times, but with sticks on the ice, we can better embrace the challenge, bend without breaking, and appreciate what makes good times great.

As we give thanks, keep your stick on the ice by recognizing how special each micro-moment is, as they compile into our own macro-moment called life. Happy Thanksgiving!

Intrinsic

We all have bad days. When they string together, the stress gets heavy. This mental weight becomes especially unwieldy when the cause is unclear. After a couple down days, I went searching for the origin of my cloudy mood.

Along with insight on entrepreneurship, venture capital, and community building, Brad Feld talks a lot about mental fitness. The entrepreneurial lifestyle is a lonely roller coaster and I’m thankful for leaders like Brad (and many others), who have helped destigmatize the complex circuitry between leadership and mental health.

I found this entrepreneurship & mental health series from Techstars helpful, then wove in this 2015 interview to translate my temporary despair. Brad talked about how he’s gone through serious bouts with depression and through those challenging times, he’s been able to identify one of his intrinsic motivations to be perpetual learning. He went on to describe how even when he was busy and perceived to be successful, if boredom began to set in, an isolating absent of joy may soon follow.

This gave me clarity. I realized that one layer of my own intrinsic motivation is also learning. I like being in situations where I’m exposed to new things, thinking about fresh ideas, solving interesting problems, hearing stories from different people, and building into things I really care about. When there’s a lull in the action, it’s easy to think the ride is over. While this thought is misguided and untrue, it’s still disheartening. Mental fitness means something different for everyone, but here are a few exercises I plan to maintain within my practice.

  • Link learning with teaching.
  • Recognize that the storm will pass.
  • Find trusted peers to release tension.
  • Use this stimuli of stress to focus.

Adam Grant reminds us that strength does not come from ignoring pain. It stems from knowing that your past self has hurt and your future self will heal. Within the crucible of entrepreneurship, hardship is inevitable. Radical self inquiry keeps leaders aware of their mental fortitude. Such awareness then helps us maintain and uncover new stepping stones that illuminate our own path to thrive beyond momentary setbacks.

Extra Shot

Calm is one of my favorite apps. The guided meditations and sleep stories are a healthy aspect of my daily routine. Here are 10 ways to boost your mental fitness, a mental fitness training guide, and free mindfulness resources from these focused friends.

Extra Credit

I have always loved listening to stories. 

At home, my parents used to tell me stories whenever I’d go to sleep. In school, I enjoy listening to friend’s and telling my own stories as well. Lately, my growing interest in entrepreneurship has me listening to people discuss their entrepreneurial journeys. These stories of solving problems and building a business have captured my attention, but I had to go beyond the status quo to find them.

Extra Shot
This caffeinated contribution was written by Ani Soni. Anirudh is a student who is becoming indispensable as he explores entrepreneurship within a startup community.

As a student in high school, there are a few classes, programs, and clubs that hint at what entrepreneurship is all about, but they lack heart, let alone the realities that come from actually building a startup or small business. I enjoy hanging out with my friends, but they don’t share the same interest I have in building my own company. My family is supportive too, but I really haven’t had a way to consistently share stories about building a business.

To fill this storytelling gap, I started looking for ways to meet other entrepreneurs. While it took a little research, I found many ways to meet people who own their own business. I’m eager to continue exploring “entrepreneurial ecosystems”, but I feel lucky to have chosen to first attend a weekly program called 1 Million Cups. Attending 1MC has allowed me to listen and learn from the stories of entrepreneurs, but showing up wasn’t easy.

I was so nervous at first! As a high schooler, I wasn’t sure if or how to show up. I assumed everyone was more qualified and successful. I didn’t think I would be able to understand, let alone contribute to the conversations. In my own mind, I didn’t belong and it was like I didn’t deserve to be there. It would have been easier to say, “maybe someday”, but I’m glad I decided to take the training wheels off.

When I arrived that first Wednesday morning, everybody was welcoming, kind, and incredibly interesting! I was thirsty to return after experiencing the generous energy this room of fellow students, entrepreneurs, intrapreneurs, and community builders exuded. Attending 1 Million Cups week after week, I now realize that people of all ages enjoy sharing stories just like me. Entrepreneurs sure like helping one another as well!

It’s only been a few months, but I already feel connected to this community of entrepreneurs. In fact, I’ve offered to join the volunteer 1MC organizing team, because I’ve seen how stories create a bond, and perhaps that’s what it’s all about. No matter where you’re at within your own journey, I’ve learned we are not alone. Everybody helps everyone grow. Now I’m on a mission to learn from more entrepreneurs, to build into my own ideas, to ask for help, and to accelerate others however I can within the entrepreneurial ecosystem.

Breakout Valuation

Breakout valuations are achieved when a business is valued based on how it makes people feel and its future potential, not just what it’s done in the past.

The nine components of a breakout valuation are confidence, vision, curiosity, people, communications, cash management, financial forecasting, capital strategy, and business design. Whether or not you sell your company, business owners who optimize in these areas, position themselves to capture a breakout valuation.

Extra Shot

This caffeinated contribution is a special adaptation from Breakout Valuation, which is the #1 New Release in Venture Capital and was written by my good friend, Patrick E. Donohue. Patrick is an entrepreneur, mentor, advisor, investor, valuation expert, and community builder who offers unique insights into the dynamics of money and business.

While you’re running a company, breakout valuations make everything easier. It attracts talented employees and quality customers. This expands your market position, makes financial capital less expensive, and invites vendors to extend better terms based on your surging trajectory.

Knowing what your ownership of the business is worth helps you make important financial decisions and becomes increasingly important as a business matures. If a business grows to the point where it becomes valuable to acquire, academic and finance professionals attempt to make valuation objective, but the complexity of each transaction makes valuation subjective in the end. Along with all the objective data, valuation is highly influenced by the environment, relationship, and personal views of the participants in a transaction. Knowing how investors and lenders use objective valuation tactics is crucial, but understanding the potential value of the business, articulating it to potential partners, and having them buy into the vision will arm you with an advantage to get what you want—a breakout valuation.

Breakout valuations are not aspirational. They emerge from what you are doing right now. It’s all about being clear with your mission and vision. It’s knowing your numbers and how everything comes together through a shared mindset, communication, and workflow. The pursuit toward a breakout valuation compounds, requiring attention today, and every day moving forward. This aggregates understanding and builds confidence. When the day comes to part with some or all of your business, the confidence from a breakout valuation will maximize the payout or deliver assurance in walking away from the deal.

Extra Shot

What are we doing today to support our goals for tomorrow?