Entrepreneurship

Co-Founders

The freedom to build as a lone wolf is exhilarating, but collaboration is how to go beyond your own limitations.

It takes more time to collaborate with others, but finding a co-founder can be life changing. Generosity, transparency, and candidness will bring the right people on board faster. Even if it’s one other person who wants to build in an aligned direction, co-founders pave a smoother path toward success.

Good people eager to collaborate can fall in your lap, but finding co-founders usually requires a concerted effort. If you hunt for the right co-founder in the beginning, it will take more time to make early progress. The trade-off is more creative and cultural alignment when things come together. This makes it easier to evolve ideas when a team finds its groove early on.

If you’ve been building as a lone wolf too long, you may have a harder time working with a co-founder. This is because it’s difficult for others to jump on a bus you’ve been driving the whole time. It’s still possible, but a thoughtful willingness to adapt is required. If you’re merging energy with another lone wolf, take your time. Moving a bit slower will uncover the why behind what was built before the partnership. As trust grows within the team, everyone will have more freedom to make the impact they want.

No matter how you decide to join forces with co-founders, choose wisely. It’s easy to work with someone like you, but don’t clone yourself. As a fun analogy, we also don’t put linebackers at wide receiver, right? Identify what you’re good at and know where you fall short. This allows you to pinpoint people who have complementary skill sets. It will also keep you focused on finding those who can push you further. With indelible honesty, who might be fun to build with?

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Perhaps you are looking for a co-founder? Show up to where the people you may want to work with are congregating. For instance, I met two of my co-founders at 1 Million Cups. We were working on different things, but over time, our shared interests led to a business idea we decided to pursue together.

Like anything new, as a team forms, early excitement will provide a surge of enthusiasm. This will soon fade and at some point, the story of this venture will end. It’s easier to plan ahead than it is to react to problems after they arise. Talk openly about roles and how everyone wants to be involved to avoid future tension. Discussing everyone’s immediate and future commitments reduces the stress of unknowns. With professional transparency a team can also work with more sustained stability. This leads to less drama and more consistent success.

As you solidify complementary co-founders, the goal is to have everyone equally enthusiastic. Think deeply about what a fair equity and role distribution means now and how it can also support future growth. No matter how cap tables look, co-founders expand capabilities and add valuable accountability. Working with others to achieve a shared goal is also more fun than working alone. Collaborate with remarkable co-founders and you’ll enjoy the ride together.

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Want more? Check out the Team chapter in You Don’t Need This Book!

By Ben McDougal, ago

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