Fun

First in Line

There’s something special about being first in line.

Being at the front of a line means you’re committed. You’ve made some form of sacrifice to ensure you’re first to experience something you care about. The unknowns of arriving in time to secure this coveted spot requires a concerted effort, but a sense of pride materializes when everything goes to plan. When was the last time you where first in a long line? My hope is that the wait was worth it!

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FliteBrite is bringing our beer festival app out of hibernation. Here’s the line that inspired this week’s writing.

When I think about being first through the lens of innovation, first in line is not such a desired position. Being first gives entrepreneurs a chance to take an early lead, but early leaders don’t always win in the end. The headwind is strongest when you’re in front. When your art involves creating something the world has never seen before, enthusiasm from early adopters is often met with pernicious friction. One common source of friction is the almost endless time spent educating the prevailing market. This protracted process wears on even the most resilient and exhausts resources every step of the way. Along with frictions that come with being first, without any clues from past success/failures, it’s harder to avoid potential pitfalls as well.

There’s value in a head start, but the early market leader often falls behind the innovation curve. Please, never hesitate to forge into the unknown, but remember that when you lead, others will always be chasing you. If you’re building in front, stay ahead with epistemic humility, a challenge network that invites you to be wrong by avoiding groupthink, a genuine desire to accelerate others, and bold leadership that allows intrapreneurs to stay wild. If you’re the one chasing, which is far more common, you’ll need to be innovative to find product-market fit, but it’s nice knowing there’s an existing path with fresh opportunities to champion change in an existing environment.

Alright, let’s add some sugar.

What if we don’t have to be in the line at all?

The front of any line may be a traditional way of getting ahead, but this requires time with no guarantees and you’re still relying on some else to let you in. If this activity is something you really enjoy, be conscious of how business can sometimes kill your passion, but there’s usually a way to be less of a spectator by getting more involved. One way to do this is by combining your creative skills and an entrepreneurial spirit to wedge yourself into the experience itself. This requires initiative, but volunteering, building into a side hustle, or using content creation skills can quickly become your ticket to skip the line all together.

By Ben McDougal, ago

Hybridize

Think back to when you were a kid. Remember that feeling of waking up to a winter wonderland? It’s a snow day! Fresh powder may cause mayhem for some, but all that mattered back then, was how quickly we could get outside to enjoy the day’s frosty gift.

This week we received a few feet of fresh snow. I love the feeling of a blank canvas this provides. I also like to think that one signal for success as an adult, is found in those who have not lost their childhood spirit, so when our little one gets excited about playing in the snow, I make it a priority as well.

After a rushed breakfast, we spent much of the day on a sledding hill. I found myself reflecting on the interactions of this momentary community. The actors are always different people, yet often play the same roles. You have the first-time sledders who are curious, excited, and afraid. In contrast, the action junkies are pushing to always go faster and higher. The adults are on snow patrol, but the personality that I find most interesting, are the hybrids. These are the kids who appreciate the exhilarating activity, but unite others by creating space to ensure newcomers are safe and also having fun. There’s an empathetic maturity in their welcoming enthusiasm.

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The original title was Snow Days.

Fast forward and these hybrids continues to bring things together. We see them in technology, translating nerd to normal, then back from normal to nerd. They are the teachers who inspire our next generation and encouraging children to think differently. Community builders are often hybrids too, as it takes a metaphoric spider to weave, explore, and tighten a collaborative web of actors, factors, and instigators together.

There are many other examples of hybrids connecting dots in almost any environment and they’re all valuable connectors that play important roles. When we think through the lens of complex adaptive systems, hybrids are those who can inclusively identify all that may be possible. They appreciate the entire spectrum of different parts within the system, as well as, the interactions between everything. Almost like chameleons, hybrids have the ability to take different shapes in order to facilitate positive interactions between different perspectives. When this skill is applied through a holistic, positive-sum lens, the effect can be surprisingly wonderful.

For those already hybridizing, thank you, stay curious, and don’t underestimate the limitless value you bring. For those who may not feel such a blended spirit, continue to lead the tribes you trust, but allow intellectual humility to welcome doubt. Such empathy paired with a genuine interest in collaboration, will inevitably unlock fresh ways for those you care about to achieve even more.

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This year-end Tweetstorm was epic and left behind some updates to my website, including a linked library to explore all my Roasted Reflections – https://BenMcDougal.com/Roasted-Reflections

As we reach the end of this wintry ride, I’m grateful for snow days that provide an unexpected chance to slow down. These cozy times provide us a chance to rest and have some fun, while also reflecting on all that’s good. Cheers to these mini moments chilled in our memories, but also to allowing the freeze to melt as we let thoughts pass and stay open to next.

By Ben McDougal, ago

2021 Bookend

This year has been transformative. For me, 2021 was a beautiful blend of secluded serenity, new beginnings, expanded connectivity, and milestone moments.

Iowa Breakfast Club

Everyone was thirsty for meaningful connection as the pandemic lingered. Using the transitory popularity of social audio, we fired up an experiment that invited entrepreneurs and ecosystem allies to chat every Friday morning. My role became the AM radio host as the Iowa Breakfast Club invited special guests to lead inclusive conversations on a wide variety of topics. Students, entrepreneurs, intrapreneurs, and community builders enjoyed these enchanting interactions for 30 consecutive weeks, before the group decided to sunset the sparkle. A recap of this experiment still needs crafted, but for now, I’ll leave you IBC fans with something to smile…”Rise and shine, it’s breakfast time!”

You Don’t Need This Book

The release of my first book, You Don’t Need This Book: Entrepreneurship in the Connected Era, was my brightest highlight of 2021. This was the literary project of a lifetime. The YDNTB softcover and eBook published on April 1st and it’s been a wonderful whirlwind ever since. Hearing from energized readers and mentoring more caffeinated authors will never get old and I’m so thankful for the overwhelming sense of peace this achievement brings.

Caffeinated Conversations

Educational organizations play a huge and recurring role within all entrepreneurial ecosystems. Through my work as an ecosystem builder, a focus on the Iowa entrepreneurial ecosystem generated a growing amount of conversations with students, teachers, and administrators throughout the state. It soon became time to collide statewide actors with a goal of allowing more inspired people to learn from each other while also exploring fresh ways to collaborate. What started as an introductory email chain, quickly evolved into a monthly meetup online. Together, we explore the intersections of entrepreneurship, innovation, and education by sharing quick updates and upcoming events, then we import/export knowledge by welcoming a special guest each month. Here are a few of the caffeinated conversations we’ve shared and please drop me a note if you’d like to join us in the future.

Startup Weekend

I shared this full recap of my first Startup Weekend experience, but it felt like an important happening this year, as it was a catalyst to a much more involved ecosystem development role with Techstars. We have another statewide, Startup Weekend Iowa event coming together to kick off 2022, and it’ll be neat to see how more connected hackathons can continue bringing curious people together.

Mindfulness

The peace that emerged from publishing YDNTB, creative work that feels like play, treasured family time, and perhaps my 40th birthday looming, seemingly came together to construct more space for mental exercise this year. I found myself thinking deeply about life through the lens of entrepreneurship, but far beyond business. This led to philosophic deep dives in the form of reading, writing, and an eagerness to spark more meaningful conversations. A daily meditation practice (the Calm app is great!) has also centered, relaxed, and recharged my mind, body, and spirit. I may try yoga in 2022. Not for the physical exercise, but more to expand this cerebral exploration.

Return to Travel

Along with sharing my favorite travel tricks, it was good to quietly live in different places throughout the pandemic, and then finally return to being a bit more adventurous toward the end of the year. Trips to Chicago, Minneapolis, Omaha, Kansas City, Ozarks, Joplin, Cedar Rapids, and Iowa City were fun, but the two highlights were returning to where we got married in Florida and golfing on Keystone Mountain in Colorado.

1 Million Cups

I’ve been having coffee at 1MC every Wednesday morning since 2012. Yes, that’s a lot of coffee with a lot of entrepreneurs! As a founder, 1MC was my weekly dose of innovative energy. An appreciation for this consistent gathering led to the early opportunity to lead in Des Moines for many years, and has since evolved into my current role working within the Kauffman Foundation as the Midwest Regional Rep. Today, our leadership team supports and connects 125+ communities nationwide. Over 40 of these 1MC communities are in the 12-state Midwest region (map), which equates to around 200 caffeinated community builders I’m blessed to work with in small, medium, and large entrepreneurial ecosystems. Being a 1MC organizer requires time, curiosity, intellectual humility, generosity, a dedication to show up, a willingness to have fun working within complexity, and a devotion for supporting entrepreneurs. The pandemic has taken its toll on this educational movement fueled by interpersonal connection, but this is a resilient tribe that’s uncovered a silver lining of more connectivity nationwide. There is an evolving sense of renewal brewing and with what’s to come, 2022 will be an interesting chapter in the story of 1 Million Cups. Join us for coffee any Wednesday morning, by visiting www.1millioncups.com.

Techstars

As a tech founder, I’ve always admired Techstars. When this global startup accelerator arrived in Iowa, it was a tremendous boost for the statewide entrepreneurial ecosystem. During the first year’s #TSDemoDay in 2020, I was talking with some of the founders about their interest in a place to land after their accelerator experience. In doing so, it dawned on me that we hadn’t hosted a Startup Weekend in a long time. This sparked an interesting conversation with my long-time friend and Managing Director of the program, Kerty Levy. She and I ended up crafted an innovative entrepreneurial ecosystem building role that gave me the freedom to holistically explore, support, and connect actors and factors throughout the Iowa entrepreneurial ecosystem. This ecosystem building work has been momentous, so when a position more involved with the actual accelerator emerged, it was a natural opportunity to get more involved. I joined Kerty in a hybrid role we titled Entrepreneur in Residence / Ecosystem Development. The 2021 Techstars Iowa Accelerator Class arrived in Des Moines soon after I accepted this expanded role, so it was definitely flying a plane while building it at the same time, but what a vigorous experience. We had ten different companies all building in different industries for 13 weeks. Along with working with each team, I leaned into fueling a community-driven culture with mentors and got to flex my event development skills by organizing mentor madness and a monumental #TSDemoDay that helped define our 2021 program. Looking forward, applications for the 2022 accelerator program open January 18th, so we’re talking with founders about their next moves. If your team is ready to scale, I’d highly recommend following @TechstarsIowa on Twitter, Instagram, and LinkedIn, then visit TechstarsIowa.com and hitting the green “Get in Touch” button to explore what Techstars can do for your startup.

Kindergarten

Our beautiful startup that pays in love is my greatest achievement. I’ve realized that one of the best things about entrepreneurship, is that it’s allowed me to be a #1 DAD! I’ve worked 80 hours so that I’m not forced to work 40. Over time, this has unlocked a freedom to avoid routine while providing a choice to how I spend my precious time. In fact, this is one reason why I’m such an advocate for entrepreneurship! Life is too short not to enjoy how we spend our time and I’m lucky to have spent so much of it with our little girl. 2021 brought a milestone moment for our family, as our daughter went to Kindergarten. As a highly involved parent, I found myself experiencing a pie chart of emotions. I was excited for her, but also selfishly felt a deep sense of loss. I also had mixed feelings about the educational system and how our little one would behave in her new environment. Perhaps this is what many parents feel when they first send their kids off to school, but this mangled mindset inspired the realization I wrote about in One & Only. It was neat to start that blog not knowing where I was headed, but in the end, realizing that gratitude provides peace. Kindergarten has been wonderful and this passage turned out to be a wonderful life lesson I’ll always appreciate.

YDNTB Audiobook

This was one of the most grueling, yet invaluable projects of my life. Building my own studio and narrating the audiobook version of YDNTB was fun, as recording an audiobook felt like performing art. The decision to then edit the entire thing myself is where the fun ended and the grind became real. I literally hand treated the accuracy, tone, and timing of every single sentence and all 37,456 words so that each listener would cherish a resonating experience. Grumbles aside, what kept me pushing, was the idea of having something I can be proud of for life. The YDNTB audiobook is now available everywhere and I can’t wait to hear what you think!

FliteBrite | OpenOpen | Jet Set Studio

With the landmark effort required to publish my first book and my expanding work as an entrepreneurial ecosystem builder, all three of my own entrepreneurial ventures received less attention. With a watchful eye on my personal bandwidth, I was well aware of how this impacted my diversified career portfolio. The pandemic had forced beer festivals, open houses, and live video game events into hibernation, so 2021 was the perfect time to expand the impact of my work. As the pandemic subsides, it’ll be difficult to regenerate momentum, but FliteBrite has a tasty beer festival app and incredible potential with our electronic serving system… OpenOpen is an open house scheduler expressly designed to save substantial time for home builders and real estate agents… and Jet Set Studio will always remain an epic hobby that pays.

Roasted Reflections

I’m grateful for the privilege to have consistently delivered these Roasted Reflections every week since activating this literary practice on December 14th, 2020. Along with this achievement I’m thankful for, the added layer of recapping each month’s writings into a threaded tweet (example) creates a shareable, linked index that also acts like an accountability pit stop to refuel my own potential to persevere.

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Reading helps us understand the world.

Writing helps us understand ourselves.

I hope you’ve enjoyed these weekly ruminations. This threaded relic I shared on Twitter includes ALL of my Roasted Reflections from 2021, organized by each month’s contemplative recap. I built into this shareable index all year and really enjoyed this summit before the ball dropped on New Year’s Eve.

Cheers to the wonderful whirlwind that was 2021, and to all that comes next in 2022!

By Ben McDougal, ago

Santa is Real

Humans tell stories.

Storytelling is the way we communicate and a key to humanity’s evolution. The stories we share come in all genres, but each one builds a different type of connection.

Stories often exist in the moment, but some are passed for generations. The most successful stories humans have ever told may be science, religion, mathematics, or money, but holidays may also land somewhere on this list of extraordinary, generational storytelling.

In the United States, 11 federal holidays are all observed in their own way, but Christmas (and comparable year-end celebrations around the world) creates a special atmosphere. In fact, the entire calendar and our fundamental sense of time seems to revolve around this cozy time of year. It’s when we pause to remember the year that was, and then look forward to what’s next. With such a shared inflection point, the year-end holiday season has created many recognizable symbols. Many holiday traditions revolve around religion, and just as many do not, but the legend of Santa seems synonymous with the holiday spirit. Whether you believe in Santa or not, it’s hard to argue with how well this jolly character embodies the essence of joy and generosity.

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Balancing this reflection made me feel like a scientist without a clear thesis, but watching our little one lean into the holiday spirit makes me grateful and full of pure wonder.

Our generational stories, decorations, music, events, letters, gifts, movies, and all that is the holiday season, can spark an undeniable truth. Great stories bring us together and if the result is anything close to the beautiful innocence of a child’s sparkle this time of year, I’m a believer and thankful that Santa is real.

By Ben McDougal, ago

Neon Future

I’ve always been fascinated by technology and how humanity interacts with what’s next.

Whether it’s artificial intelligence (AI), space travel, computer vision, machine learning, biotech, transformative energy, quantum computing, cerebral transcendence, or synthetic materials, math, or physics we have yet to discover, the deep future is one of my favorite day dreams. I don’t often get to talk with others about these questions we can not answer, but TV shows, movies, books, and music provide fun ways to personalize each paradox.

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Year Million, Cosmos, Altered Carbon, Foundation, and NOVA are a few TV shows that lean into what our neon future may look like. The Matrix, Ghost In the Shell, Finch, Transcendence, Dune, Ready Player Two, Interstellar, The Martian, Lucy, and Ex Machina are a few of my favorite sci-fi movies in this realm. I can’t say I’ve read many books that connect on this front, but when it comes to music, a lot of EDM feels futuristic. In fact, the inspiration for my title comes from Steve Aoki’s latest odyssey and I’ll close with lyrics to maintain this state of trance.

As I think about the future and what technology may allow humanity to achieve, my mind drifts through an eternal field of abundance. Our destiny will naturally change the future of work. My hope is that instead of stealing jobs, the heightened infrastructure will advance our kind and provide more humans the chance to scrutinize their own creativity. Instead of worrying about turning a knob all day, society can focus more on what the turning knob accomplishes.

It’s hard to reflect on such vast unknowns. It’s even harder to find closure. This doesn’t do the trick, but one interesting question that I’ve asked many people, is “does everyone have an entrepreneurial spirit?” I’ve been surprised with how many people say no, but one of my favorite responses included a thoughtful caveat. Perhaps everyone has a creative spirit, but those who are able/willing to tolerate risk, unlock the opportunity to decipher their entrepreneurial spirit.

That said, when it comes to this discourse, I’m interested less about business, and more about the enjoyment of deep thoughts, interesting conversation, and pure wonder.

There’s light years more to unpack here and this was never meant to be a scientific summary. Think of this flickering spark as more of an invitation to cut loose for the neon future is entirely unpredictable, expect for one thing: that before you know it, the neon future, will be the past. Stay wild my friends!

Life has limitless variety
But today, because of aging, it does not have limitless scope
In the neon future life will have opportunity to explore its limitless diversity
Life will have no boundaries

By Ben McDougal, ago