Entrepreneurship

#1 DAD

Little startups that pay in love are a blank canvas that comes to life through you.

By nature, parents want to provide the means for children to go beyond their potential. As entrepreneurs, when we see the best of ourselves in someone we care so much about, a sense of renewed purpose often emerges. To celebrate Father’s Day, here are a three parenting tactics I’ve found especially interesting.

You’ve Got Mail

Secure an email for your little one, then use this communication channel to write to them as they grow up. Whether you start writing before they are born or begin this practice later in their life, imagine what a gift an inbox full of thoughtful updates will be in the future! This new email can be shared with family and used for future account setup if you want, but at a minimum, you will have created a personalized time machine.

Along with all the sentimental content you’ll deliver someday, your kids will appreciate having a solid address to use as their primary email someday. Such a preferred email address may not be available years from now, so I’d suggest securing something they can use long after childhood. For example, [email protected] is a safe place to start and while you’re at it? Perhaps it’s a good time to register a domain in case they ever want to build on their name.com.

They Grow Up

Similar to how death can inspire us to live, recognizing that kids will grow up, reminds us to enjoy everything about each moment. Everyone tells us to cherish the simple joys of life, but it may be worth getting a little extra creative. One way to enhance your family’s ability to relive memorable moments, is by using multimedia marketing skills to tell family stories in a way that makes memories easier and more fun to revisit. Most people have an endless collection of photos/video on their smartphone, but scrolling around a digital device doesn’t translate into something a group can enjoy together. As we all know, it’s easy for good things to get lost when there’s so much noise as well.

Your future self will thank you when you spend the extra effort to organize content outside of the latest social media platform. This attentive, pro-active organization will also make relics easier to craft. Whether it’s a photo slideshow you put together each year, a fun collection of audio recordings, something printed that sits on the shelf, or a video edit that highlights your adventures, the time spent compiling these legacy projects will rarely feel wasted.

Avoid Routine

“Time flies” and “they grow up so fast” is accurate, but I’m convinced that avoiding routine may slow down time. The freedom to be spontaneous is a privilege and everyone will define such freedom differently, but a proven path to explore such a reality is entrepreneurship. Boundless hard work, dedication, and resiliency are what it takes, but our own suffering provides a stronger sense of purpose and the chance to enjoy more treasured time doing things that make us happy.

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What’s your go-to parenting tip? Share it as a comment or hit me up!

The time and energy family life requires is immeasurable, but as the love from your kids somehow unlocks more hours in the day, new perspectives form and fresh motivation is released. Perhaps a reward for parents who lead by example is the opportunity to share everything with those who matter most.

By Ben McDougal, ago

Lone Wolves

A common misconception is that you must have a team to be successful. There is a limit to your own capacity, but it is possible to build rewarding endeavors all by yourself. Solving complex problems may require co-founders and a larger team, but your passionate dedication is all you need to get started.

Lasting energy is required to forge this path, but without the need to answer to anyone, you can stay nimble and be more efficient by eliminating internal delays. To avoid burnout, you must stay mindful of your personal bandwidth. Self-awareness will help you avoid market disconnects, The Headline Trap, and relationship problems as well.

To coordinate new initiatives into your career portfolio, consider how the project connects to your current work. Clear overlaps can be good, but can also cause unwanted tension. A project less related to your existing work actually makes everything easier to shuffle. Even when projects affect different industries, it’s still you making things happen. The option to build into what motivates you in different ways will energize your work on all fronts. Action on one project will provide fresh momentum for others. Learn when to say yes and no, then wisely activate your time on each front.

As a lone wolf, it’s easy to go hard toward your own dream, but know when you need help. The freedom of working alone is within reach, but execution still requires collaboration. The world is full of friends, community allies, and contractors eager to help. Outside assistance may slow you down, but it won’t dilute equity, and it may be the key to a new reality.

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

If you venture out alone, prepare for intoxicating highs and crushing loneliness. The consuming nature of building by yourself will incite grit, but don’t let it blind you. It’s easy to build too far into the wrong direction without a team. This is why community and customer discovery are even more important for lone wolves.

By Ben McDougal, ago

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