Entrepreneurship

Weekend Sprint

We just wrapped up Startup Weekend Iowa.

This was an online event, so our organizing team compressed what is normally a 54-hour, localized, in-person hackathon… into just 26 hours of people talking, typing, working and connecting together without the barrier of location.

Thanks to our own Wizard of Oz, virtual interactions were seamless and I was set free to creatively facilitate this high stress, no risk experience. It was energizing to have 25 participants and 15 mentors connecting to build two companies that pitched head-to-head for esteemed judges on demo day. This was a statewide event for Iowa, but the international element was in full effect as we also had new friends teleporting in from Canada and India to participate. While most of the event was hosted in a private platform that we called “the venue”, here’s a YouTube link to “the stage” where our keynote kickoffs and demo day were live streamed.

These weekly reflections, which I’ve been calling Roasted Reflections, are purposely timeless, but I share this brief event recap because it reminds me how easy it is to build when only a few people decide to work together. Yes, in-person gatherings create more random, serendipitous interactions, but I continue to marvel at how new interactions can be so efficiently ignited through these online interactions.

This was actually my first Startup Weekend experience! In the past, I convinced myself that my career portfolio was too full to build yet another new company. The infrequency of a local event and the anticipated time required were also factors in my past decisions, but now I realize, this combination of considerations led to a misguided assumption.

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You hear this tweetable thought often, but smart people change their minds all the time.

Startup Weekend can be a place where participants come together to build a business idea into reality, but it can also be a wonderful chance to catch up with friends, learn a new trick, mentor people exploring their own entrepreneurial spirit and/or simply observe some magic in action.

As one of the organizers and lead facilitators, I enjoyed a front row seat that allowed me to commentate the weekend while helping two teams build ideas into reality.

The energy of this weekend sprint was remarkable, but I noticed something as we all sat back and virtually celebrated demo day over a few brews during afties. It felt like the last day of summer camp. Everyone had been working alongside each other and while closing things down felt bittersweet, you could tell everyone appreciated the opportunity. This group had done something they were proud of and there seemed to be an unspoken premonition that Startup Weekend was not the last time these starters, makers, doers, and dreamers would come together to collaborate.

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Building alone is easy. Find friends to make it fun.

By Ben McDougal, ago

2 Hours

Greg Horowitt is a social architect and pracademic. He is an accomplished entrepreneur, investor and global advisor. I always knew of Greg because he co-authored The Rainforest with Victor Hwang. After years of learning from Victor, I decided it was time to connect with the other half of this intellectual equation. I reached out to Greg and he was generous enough to setup a time to chat. We had no agenda, but ended up talking together for two hours!

This extended discussion allowed me to enjoy fun anecdotes about a bestseller so many entrepreneurial ecosystem builders have on their bookshelf. I learned about Greg’s innovation design role at UC San Diego and his upcoming book about the religion of innovation too. We riffed on entrepreneurship, venture capital, innovation ecosystems, complex adaptive systems, how humans think, economic development, the speed of trust and how storytelling brings everything together. Here is a Twitter thread with our photo and a few more memorable moments, but having Greg Horowitt lob knowledge grenades my way was such a treat.

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Meaningful discussions can form faster without an agenda.

This enlightening interaction has me reflecting on how a hint of initiative unlocked another cool connection. Also, how that extra hour gave Greg and I time to discuss a variety of topics with space for this thoughtful exploration to go deeper. Look at your bookshelf or social media feed. All of us have giants we’d love to meet. Do you seek out learning sessions with people you admire? How might a significant conversation evolve if you give it an extra hour to develop?

We’re all busy, sure, but a peculiar conversation is rarely a waste of time. Perhaps it’s only done occasionally, but more cerebral conversations allow us to go beyond protecting our knowledge with fancy jargon. Perpetual learning with a coexisting effort to accelerate others will release innovative energy that sparks creativity and reveals a path to deconstructed understanding.

By Ben McDougal, ago

Pure Wonder

Children embody a state of wonder that entrepreneurs can learn from.

They wake up each morning without a plan. They have no preconceptions. No judgments. No worries. A lack of expectations allow kids to naturally live in the moment. They get excited about the little things and cry over nothing. Their states of pure wonder is fascinating.

Now, fast forward 20 years. The world hardens us. We want to impress and make our mark, but life can feel exhausting and the need to make ends meet adds constant stress. Our experiences make us more intelligent, capable and aware of our surroundings, but they also limit our ability to feel pure wonder.

As you’re building a business, release from the daily grind by thinking like a child. Pretend you were born yesterday. Be silly once in awhile. Forget the agenda. Color outside the lines. Get weird to solve problems. Laugh at your mistakes. Play in your sandbox and have fun getting messy. Let a child-like sense of wonder shrink your ego to make room for what’s next. What you’re building matters and if your work allows you to feel pure wonder, be thankful and pass it on.

By Ben McDougal, ago

Personal Bandwidth

New projects make work invigorating and it’s fun building things we care about. When we’re all able to do so much more with less in our connected era, the danger becomes how easy it is to spread yourself too thin. If you seek to unlock the boundless energy from a balanced career portfolio, it’s critical to keep an eye on your personal bandwidth.

To make it easy, visualize all the work you do as a dynamic pie chart. Each project you’re involved with represents one slice. It’s not an exact science, but the more time, money and energy you spend on something, the larger that slice becomes. Let’s call this your career portfolio.

Most of us can manage multiple slices of activity within our career portfolio. For example, a traditional, salaried position may be the lion share, but there’s still room for that innovative idea at your company, a little side hustle, the volunteer role and mentoring a few other entrepreneurs. No matter what makes up the complete pie chart, stay mindful of the coevolving sizes of each slice and how everything interacts within the overall system.

Saying yes or no to new projects should obviously be carefully considered. As you make these decisions, be honest with the resources required to continue building on each front. The time you spend on one thing can’t be spent on others, but positive force in one area often fuels fresh energy (and clarity if it’s time to quit) for other areas of your career portfolio. When different projects are in the same realm, synergies may be easier to compound, but sometimes having projects in completely different industries provides stabilizing diversification.

Beyond the obvious impact of adding or removing elements within your career portfolio, how resources are spent on existing areas of your career portfolio should feel strategic. Think about how much time is being spent compared to the income that’s being produced. There are other factors to consider too, as we know it’s not all about the money. Reflect on the type of energy each project generates. Who do you get to work with and how does the work make you feel overall? Hobbies that pay just enough to break even, leading a group of people you care about or volunteering to become a mentor are all wonderful examples of satisfying additions that don’t pay the bills.

Have something that’s dragging you in the wrong direction? It’s hard to revive old projects, but don’t be afraid to put things on the back burner. That said, if it is time to quit, read The Dip by Seth Godin, then decide if and when to make your move. Winners quit all the time, they just quit the right things at the right time.

That last sentence reveals one more important variable: good timing. When you activate new projects, adjust resources or quit something to make space for what’s next, good timing will provide a noticeable blend of confidence and tranquility. This state of mind will allow your work to make a bigger impact. To give yourself room to find good timing, remember entrepreneurship is not a race. Urgency is helpful because it creates valuable momentum, but stay patient knowing that persistence is the ultimate wild card.

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I once had a boss tell me I could never catch two rabbits. That’s outdated. With a balanced career portfolio and the support of those around you, we’re all able to catch more proverbial rabbits without diluting ourselves to mediocrity. Learn to efficiently activate different energies, on different projects, with different people, at different times, that all connect through you.

By Ben McDougal, ago

The Headline Trap

Reducing barriers to entrepreneurship allows more people to feel inspired by their work. There are many common barriers to entrepreneurship. As I’ve worked with students, new entrepreneurs and intrapreneurs working inside existing companies, I’ve noticed a self-limiting ideology we can call The Headline Trap.

The Headline Trap is an emotional barrier that can subconsciously make people think their own entrepreneurial abilities don’t warrant action. It festers from the deception that business ventures must “go big” or make a bunch of cash to positively impact one’s career portfolio.

This is no surprise. Successful startup stories are celebrated loudly. These spotlights are well deserved and celebrating entrepreneurs is important, but you don’t have to build something crazy to feel the innovative energy of entrepreneurship.

Everyone has a product or new initiative they’ve thought about exploring. Yes, building a business that impacts a lot of people is absolutely possible, but we’re all invited to tinker. Side hustles, community building, volunteerism and innovative projects that intrapreneurs spark inside existing companies all represent entrepreneurial efforts that should be celebrated.

Need someone to bounce ideas off of? Let’s have coffee.

Any project you care about generates genuine energy. This energy is commonly referred to as passion. The beauty of passion is that it leads to persistence. As you find ways to create joy, you’ll savor the project longer. Even if you’re not making a profit (yet), you can still be inspired by the process. This inspiration often transcends into other areas of your career portfolio as well. In fact, sometimes an entrepreneurial venture is less about the money and more about the opportunity to collaborate with others. Working with people you enjoy being around is a treat and finding trusted partners with complimenting skill sets is the trick to make things even more interesting.

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Building a business with less concern about revenue can provide a sense of peace, but beware, the luxury of not needing something to work can lead to crippling procrastination. Maintain transparency with everyone’s commitment levels to avoid tension.

Even when a project is only a tiny sliver of your career portfolio (we’ll talk more about managing your career portfolio next week), curiosity is being triggered. Not everyone will identify these actions as entrepreneurial, but innovative energy is being activated. Whether a project works or not, the entrepreneurial spirit gets bolder with time and often leads to more innovative initiatives in the future.

This type of personal growth also creates expanded interest in the startup and small business community. At the community level, entrepreneurial ecosystem builders can help people avoid The Headline Trap by recognizing, encouraging and celebrating projects that don’t make the news. This benefits everyone when more passionate people are invited to plug in. As more curious people are connected throughout the entrepreneurial ecosystem, take the opportunity to be radically inclusive to fuel a more diverse, flexible and sustainable environment.

By Ben McDougal, ago