Entrepreneurship

Wayfinders

Startups that pay in love are a blank
canvas that comes to life through us.

By nature, parents want to provide the means for children to go beyond their potential. Family requires immeasurable resources, but the love from our kids unlocks more hours in the day. The added productivity comes from seeing the best of ourselves in someone we care so much about. Purpose is renewed and the heart we put into our creative work can make our presence as parents even more interesting.

Summon Stories

Children grow up fast, so we stay in the 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 summon family stories.

Every moment is special. As creation becomes second nature, handpicked memories can be stitched together to revisit interactively, any time, with or without you.

Most of us have an endless collection of photos and video on our smartphone, but scrolling around on a digital device doesn’t translate into something a group can enjoy together. It’s easy for good things to get lost in so much noise and spoken storytelling is always merry too, but why not paint more stories with a few added brushes?

Quiet relics like photo slideshows, something printed that sits beautifully on the shelf, a mix of audio recordings, art on the wall, or a cinematic feature film that highlights your adventures. You’re the creator with endless ways to create.

We all do a form of this, because family is our favorite, but the time required is real. A rigid cadence is not required, since any day is a good day to ship this type of of art. In the early days of photos and video, it was only birthdays and Christmas — now everyday is a holiday. No need to rush, but keep producing new surprises. Everyone will love the end result and as more come together, the growing playlist becomes a sequence of stories that follow kids growing up. With our constant collection of content, a good story is always ready to tell, but at a minimum, why not share an annual gift with your kids, partner, and other loved ones?

Along the way, attentive and controlled organization will make a growing collection of relics easier to craft. This takes an ongoing commitment, but file management is easy and helps bring life to life with shared memories.

Your future self will then thank you for an effort to organize this heartfelt content. Share in public if you want, but that can alter the art if it becomes a show. Do it for yourself and your favorite people first. Organize what will be a massive library offline, then, if you want play with the transitory channels of social media, that’s a personal choice.

No matter who resists whatever it may be, time compiling legacy projects will rarely feel wasted. It’s using our real skills to commemorate those we love. Scanned memories may give us content without capturing it in the future. For now, it’s up to us to trap time for personal storytelling.

Compensation is not money, but this does enhance your content creation skills for other areas in life. Technology also makes editing content more productive, but this is not your average task. This is the type of sincere storytelling you enjoy spending time with.

As kids grow up, these projects will have the lowest view counts, but always be your very favorite. Looking ahead, it’s crazy to imagine being a child right now, then receiving such a gift from my parents someday!

You’ve Got Mail

Consider setting up an email for your little one. This inbox can be used as a communication channel to write to your child as they grow up. Whether you start writing before they are born or later in their life, imagine what a gift this inbox will be in the future! This email address can be shared with family and used for online accounts if you want, but at a minimum, this curates a personalized time machine full of thoughtful updates.

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

Along with sentimental content, your kids will appreciate an email address that can be used after childhood. First and last name with your preferred email provider should stand the test of time. This is also a good chance to register a URL using their first and last name. This can connect to their email or support a personal website someday.

Avoid Routine

“Time flies” and “they grow up so fast” is accurate, but avoiding routine may slow down time.

The freedom to be spontaneous is a privilege and everyone will define such flexibility differently, but a proven path to explore such a reality is entrepreneurship. Boundless hard work, dedication, and resiliency are what this lifestyle takes, but suffering provides a stronger sense of purpose.

As this purpose is layered in later stages of life, experiential wisdom can be channeled into more treasured time doing things that make us happy. While hardship is part of the deal, children make their parents happy. 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 Hack

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