Ben Sinclair is a wizard who builds amazing technology just for fun. This episode is hilariously awesome as The Bens chat about their special origin story. We open the gates on the evolution of FliteBrite, building an electronic serving system, and a beer festival app. Laugh with Ben and Sinclair as we have fun connecting jokes with WWDC23, astronomy, web2 vs. web3, OpenOpen, being present as a parent, building as co-founders, and staying professional over pinball.
This year has been transformative. For me, 2021 was a beautiful blend of secluded serenity, new beginnings, expanded connectivity, and milestone moments.
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!”
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.
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.
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.
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.
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.
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.
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.
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.
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!
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.
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.
Extra Shot
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!