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

Career Nirvana

Career nirvana is achieved when your community, work, and personal life are in harmony. This state of mind comes from happiness, health, and wealth emanating from the freedom to do whatever you’re best at with people you care about.

There is little holding you back from achieving such splendor. Start by doing remarkable work you enjoy. This creativity earns attention and delivers intellectual, human, financial, network, cultural, physical, and institutional capital. As we learn from The Startup Community Way, the Seven Capitals keep you building by using what you have, to attract what you want.

Let passion fuel persistence, then fuse your career portfolio into the entrepreneurial ecosystem. As you connect into community, be generous by accelerating others and use the trust that creates to do it more often. When this becomes routine, your generosity will leave a legacy. For innovators looking to change the world, such a legacy grants enduring satisfaction and furthers the sense of euphoria.

As a fulfilling career is composed, it’s easier to find work-life balance. Remember, we work to live. We don’t live to work. Nobody looks back wishing they had spent more time in the office. Use the freedom you create to embrace those you love while doing more things that make you happy.

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“The peace and satisfaction of building what you truly care about is one of life’s greatest gifts.”  –You Don’t Need This Book

This may sound idealistic, but it’s not all rainbows and unicorns. This approach to work requires creativity, immeasurable time, immense ambition, and advanced efficiency. As discussed in the Side Hustles chapter of YDNTB, an acute awareness of your personal bandwidth is essential to optimizing when and how resources are utilized. It can also be tempting to spend too much time on things that are fun but may not have real potential. Be humble enough to recognize what you have and what it will take to evolve your idea(s) into reality. Managing multiple “hobbies that pay” takes serious effort, but the reward is extraordinary work you love talking about and an inner peace that provides transformative happiness.

If you achieve career nirvana, be thankful, but recognize that things will always change. What you have today may not be the same tomorrow. Keep building to enjoy the moment, then make it last with generosity that recycles a sense of abundance for others along the way.

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Cheers to everyone who made last week’s book launch a huge success! Signed softcovers were shipped nationwide and more orders continue to pour in. As you dig into YDNTB, I’d love to see photos, hear what resonates and explore fresh ways to accelerate your work.

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

Love Triangles

As we celebrate our love for one another, Valentine’s Day felt like a heartfelt time to reflect on building a business with and around members of your family.

The permanence of family leads to many business partnerships. Some operations pass from one generation to the next. Others spawn when family members decide to start something new. Still more businesses come together as people create new family bonds and merge their work into love triangles.

It seems obvious to start something with those you love. In some cases, the convenience makes it easy. In other cases, it can become a necessity to turn the family into a team. No matter the why, transparency and trust within a family is hard to beat. This allows family members to wholeheartedly lean on one another. Such an unwavering ability to count on each other is why family businesses always have a chance.

While family businesses can thrive for generations, there are dangerous downsides as well. Not everyone who loves each other should work together. Home and work are often like night and day. The difference between the two makes each one better. Living and working with family makes it hard to separate the two. This can lead to arguments that extend far beyond the office. These inescapable emotions can damage relationships and bleed into the broader team. While you’ll spend the most time with your family, building a life together doesn’t mean you have to work on the same thing. A healthy amount of individuality allows each person to do more and space makes coming back home even sweeter.

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Do you work with family? If so, share your best tips in the comments! Also, did you know Brad Feld and Amy Batchelor wrote an entire book on this, called Startup Life?

Whether you build a business together or not, family dynamics affect all entrepreneurs. The most direct impact comes from your significant other. Your co-founder in life has a huge influence on your ability to thrive as an entrepreneur. Almost like separations of power, each person can provide contrasting perspectives, honest feedback and valuable support to balance the time, financial and emotional responsibilities of life.

Co-founders in life who share authentic trust give each other stability, fewer restrictions and more opportunities. If you find the love of your life, help them be their best. Admit they are the better half and be humble enough to let them return the favor. Such motivation from inside the home fuels a deep sense of abundance. The result is a more determined mind, body and soul eager to learn from the person who knows you best. This constant support brews loving vibes that spill into your work. Two people who push each other to be better than they would have been alone is the ultimate gift.

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To love is to share life together,
to build special plans just for two,
to work side by side,
and then smile with pride,
as one by one, dreams all come true.
The Meaning of Love – Krina Shah
By Ben McDougal, ago

Super Sentence

Modern gladiators went to battle last weekend and it only took around 11 minutes for the Tampa Bay Buccaneers to win Super Bowl LV. It’s interesting to compare such a small window of actual gameplay to the endless pregame analysis, commentary, predictions, production and post-game highlights.

With two weeks leading up to game day and another week highlighting this annual event, the Super Bowl experience basically lasts three weeks. That’s up to 30,240 minutes of potential attention the NFL can earn from each consumer. With those 11 minutes of live action only representing 0.04% of this three week long spectacle, clearly the Super Bowl is about more than professional football. It’s about the host city coming to life, a stadium full of fans, the TV commercials, the halftime show, the food and everyone sharing the Super Bowl together.

This is not by accident. The NFL understands their audience. They’ve achieved product-market fit and since 1920, have built around what they do best. This entertainment behemoth does American football really well, but $15 Billion in annual revenue doesn’t come from 150 snaps per game. It comes from being the best at one thing, then expanding on that with complementing (and profitable) activities. This has strengthened their existing fan base, created opportunities to increase their audience and transformed their product into a cultural phenomenon.

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If your company was given a free Super Bowl commercial, who would be your target audience? What story would you tell? What action would you want viewers to take and would you be ready to convert attention into trust when they took that action?

The NFL makes product-market fit look easy, but building something that satisfies true demand is harder than it sounds. Avoid getting sacked by admitting your idea isn’t special and that the future of your business relies on your ability to consistently execute. Trust that early success relies on clarifying your value proposition, evolving your business based on continued customer discovery and your ability to collaborate with those around you. This takes finesse, thick skin and a special combination of urgency mixed with patience, but as you secure more paying customers, you may be given a chance to broaden the impact.

Can you describe what you and/or your company does best in one sentence? Hit me with it! If you send me your own super sentence, I’ll connect you with someone who can get you to the next first down.

By Ben McDougal, ago