Entrepreneurship

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.

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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.

By Ben McDougal, ago

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.

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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.

By Ben McDougal, ago

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.

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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.

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

By Ben McDougal, ago

Ask For Help

I was raised to “go figure it out”.

This DIY mindset was reinforced through years of education and employment in traditional, corporate environments. If there was a problem that I didn’t have the answer to, I would naturally slide into problem solving mode to independently determine different ways to ensure progress. By and large, this mindset has served me well. It has taught me to be resilient in the face of challenges, even when it’s not the popular path forward. It’s left me with an open, achievement-oriented approach with less limitations, because I am a DIY business woman.

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This caffeinated contribution was written by Laurie Brown. I had the pleasure of collaborating with this operational savant through her work inside the Kauffman Foundation and with 1 Million Cups. Laurie is now helping fellow founders optimize their own business operations, so let me know if you’d like a warm introduction.

Lately, I’ve been re-thinking this approach. Perhaps my DIY mindset should include more asking for help?

Within a recent career transition, I’ve been exploring this new attitude through an experiment. On numerous occasions, I’ve encountered unknowns. In these moments of uncertainty, I’ve resisted my life-long instinct to figure out every answer on my own. Instead, I have started asking myself, who in my network might be able to help me learn?  As this experiment has unfolded, I have three key takeaways.

  1. Asking for help drives results. I can learn from others who have pioneered effective solutions, which saves me time (and pain) along the way.
  2. The collaboration from these exchanges go beyond the problem at hand. Many times it strengthens relationships, the fun of helping each other forms friendships, and mutual professional growth is a welcomed side effect.
  3. By leading the way to ask for help, I serve as a role model to my peers and open the door from them to ask me for help in return.

My DIY ways will continue to serve me well, but I’ve learned that an added dose of curiosity and willingness to listen can add fresh layers of potential. I’ll continue to carry forward my resilient, solution-driven approach, but plan to incorporate more inclusive problem solving and an “AFH attitude” within my engaged network. This will keep problems from staying problems, while also creating a new catalyst for prosperity.

By Ben McDougal, ago

Bloop

Imagine yourself as a circle.

It’s tempting to suggest a sphere, but the added dimension is not necessary for this metaphor. Alright, with your circular self, take a tiny portion of the arc and “bloop”… push it beyond the circle’s circumference. Even the smallest nudge gives the entire circle space to expand.

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I had fun making all sorts of sounds as I considered the title for this reflection, but I’d love to hear how you’d describe the sound of such an expansion. Also, since I had to look up the terms to ensure this metaphor was translated correctly, here are the parts of a circle.

There’s plenty of research behind the idea of small improvements adding up. As we hear from inspired speakers and read about in Atomic Habits by James Clear, if you get one percent better each day, you’ll end up thirty-seven times better by the end of a year. It’s hard to define “better” and such steady progress would surely require sacrifice, but most will agree that small choices don’t make much of a difference, until they add up.

While establishing systems that support good habits and compiled improvements are great, this reflection is more about welcoming singular moments of exploration and growth, even when it seems unrelated, weird, or insignificant.

Perhaps it’s trying something new without preconceptions, saying yes when no is status quo, or being the initiator when movement is seen as risk? As we poke the box and invite a bit more bloop in our life, we give ourselves an opportunity to grow as our own circles expand.

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To thank those who have enjoyed brewing on these Roasted Reflections every week for almost two years AND to say hello to some new friends, here’s a free gift just for fun!

By Ben McDougal, ago