Techstars

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

Life’s a Pitch

Humans are innate storytellers. We use stories to relay understanding. Whether it’s a caffeinated conversation, a business networking event, dinner with friends, or on-stage in front of others, entrepreneurs must be able to translate the story of their business to anyone.

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Pitches are built to impress. Presentations are meant to share. One size does not fit all. Consider the environment, audience, and format to cater how your story is told. Preparation that includes thoughtful awareness will optimize engagement.

Startup founders and small business owners should be able to pitch in any situation, on the spot, and without props. There are many templates that highlight key areas to include within a pitch, but the overall objective is to deliver a lasting impact in the least amount of time. Honest enthusiasm, transparent vulnerability, and concise simplicity are great ways to accomplish this. To prepare for any audience, it’s wise to craft a few different versions of your story. Here’s a collection to consider:

1 sentence – Sharp conversation starter.
42 seconds – Ideal for concise intros in a group setting.
6 minutes – Time to deliver enough detail needed to support valuable Q&A.
10 minutes – Room for more details, but be careful not to numb the audience.
1 hour – A talk meant to deliver value, with details of your business included.

Slide Deck Design

When a slide deck is part of the equation, take full advantage of this opportunity. Building a slide deck establishes the cadence of your performance. Slide decks should create flow while supporting your verbal presentation with clear and impactful visuals. Slides should not include full sentences or too many bullet points for you to read aloud. Titles or short phrases may help guide the audience, but great slide decks use very few words. When it comes to slide deck design, keep transitions between each slide simple, but consider how content comes and goes on each slide. Subtle animations and thoughtful hints of movement will help you stand out without being too distracting.

With a remarkable slide deck in place, practice your presentation and sync it to the timing of each slide. Whether you use animated content or not, it’s best to have a single click to move between each slide. On stage, your attention should be on connecting with the audience, not the slide deck or the clicker.

If questions are allowed after your speak, consider including supportive back slides. Back slides are placed after the final slide. They are used to highlight material not included in the main presentation. Handy back slides include detailed pricing, competitive analysis, marketing strategies, research data, and intricate financial information. People who understand what they’re talking about can use fewer words, and back slides allow you to deliver a strategically simplified presentation. For the audience, this reduces the numbing effect of information overload. With back slides ready, you can indulge in clarifying conciseness. This makes for a more impactful tone. It can even be good to purposefully leave out a curious topic from the main presentation. When the inevitable question pops, you can use the sneaky back slide to share a more focused response. Memorize the order of your back slides and you’ll soon be leading a more authoritative exchange. In short, back slides prove you’re a pro.

To complete your slide deck preparation, export everything into one PDF and create a JPG file for each slide. The richest presentation will always come directly from the software (I prefer Keynote) a slide deck was built from. The PDF and JPG formats can be used as shareable marketing materials. More important, they are quick substitutes to counter any sort of last minute technical issues. Deliver the digital assets on time and organizing everything on a flash drive, just in case.

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Business pitch competitions and grant programs are a good way to financially supplement your business without diluting the equity structure. For example, when we were first building FliteBrite, we won a $10K pitch competition and earned a $25K grant from the Iowa Economic Development Authority.

Being prepared is obviously important when all eyes are on you. Memorize the order of your slides, but not what you plan to say. Memorizing a pitch word-for-word is safe for some, but a more genuine tone comes from the heart. We’ve all seen people lose their place in a memorized script or fumble through notecards. Avoid this embarrassment by practicing what you plan to say out loud. The mirror at home is a fine place to start, but nothing compares to a live audience. The sentiment of your pitch should remain consistent, but it won’t sound the same each time. As you tell your story, feedback from people you don’t know will sharpen the business and help you continuously evolve your transmission.

By Ben McDougal, ago

Pain Relievers vs. Vitamins

Think about the last time you were really sick. In those moments of agony, consider how much you appreciate pain-relieving medicine made to ease the torment. Most of us don’t hesitate to buy solutions that ease our pain.

Now, think about a time when everything was going your way. You may take vitamins to support a healthy lifestyle, but if you miss a day, who cares, right? Think about your medicine cabinet. For every vitamin you routinely take, how many others sit on the shelf collecting dust?

Vitamins are good, but pain relievers are great. This is an analogy we can bring into business. As you consider your product/service, are you providing something that solves the pain of a target customer, or is it a nice-to-have that may (or may not) provide clear value?

If you’re unsure, you probably have a vitamin. If people like the idea, but hesitate to buy, you probably have a vitamin. If you always find yourself explaining why someone needs what you have, you probably have a vitamin. How can such assumptions be made? Pain relievers are easy to spot. They sell as fast as the supply can keep up with demand.

Ready to mutate a vitamin into a pain reliever? Ongoing customer discovery is the best way to keep a pulse on your company and helps entrepreneurs build toward sipping from the holy grail: product-market fit. As you ease the true pain of your target customer, stories that sell (marketing) highlight how you do so. Forget the impressive jargon. Lean into the pain.

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Unrelated to this week’s reflection, I love local bookstores. I always spend more than I’ll ever make in sales of my own book on their shelf, but these places are just so cozy. It’d be hard to get rich, but the wealth of owning a bookstore must be endlessly rewarding.

By Ben McDougal, ago

Mentor Madness

Mentors help entrepreneurs without asking for anything in return.

These diamonds in the rough may be hard to find and the vulnerability to ask others for help can feel heavy, but don’t be afraid. Most entrepreneurs and intrapreneurs enjoy helping others. Not everyone is graced with extra time, but there are good mentors in every community. Local mentors provide huge in-person value and the online universe offers infinitely more ways to find good fits. The wider your engaged network is, the more strategic you can be when selecting mentors as well. Even with a wide spectrum of options, take time to consider whom you trust and who will trust you in return. Be respectful of everyone’s time, but don’t be afraid to approach the giants you admire most.

As an entrepreneur talking with potential mentors, be transparent about your situation, concise with storytelling, and clear with specific needs. Spell out your vision, the current state of your business, what makes you a pain reliever vs. a vitamin, and how this mentor’s experience could help you navigate the fog.

As you explore mentor relationships, it’s unlikely one person can support you on all fronts. This means you must get comfortable working with multiple mentors.

The more one mentor can help, the more attention they deserve. When you give a mentor more attention, it should not feel like they need to do the same. Approach each exchange with composure. Make it convenient for people who aren’t required to care. Go out of your way to be effective and efficient. Learn how someone likes to communicate and make detailed emails concise. Answer questions directly and find ways to keep connecting new dots. Think about deliberate deliverables. As things come together, slow play the delivery of assets and things you want to discuss. This will keep progress from feeling too heavy. It also creates space for concentrated feedback on more specific topics. A mentor who helps you in a meaningful way will rarely disappear, so there’s no need to overload them with too much at once. This practice helps you stay on top of ongoing conversations, while also allowing mentors to add more precise value. Optimizing mentor relationships this way will inspires trust, action fueled by accountability, and solidify a lasting sense of accomplishment for everyone interested in your success.

Along with learning from mentors, consider being a mentor yourself! Success (and failure) leaves clues so no matter what you’ve achieved in life, you have wisdom to share.

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Interested in mentorship? Here are characteristics to consider.

If you decide to offer your time in this way, be generous, but also realistic about how you can help. Mentoring can become a nagging task if you’re stretched too thin and the moment you feel resentment, the quality of your support diminishes. To avoid this pitfall, be upfront with the time you’re willing to commit and deliver whatever is promised. When volunteering a significant amount of time, be sure to feel at peace about the impact you’re making.

Your time spent mentoring should feel easy, efficient, and fun, yet challenging and rewarding as well. A #GiveFirst mindset paired with an authentic connection to founders you care about creates space for honest feedback and a magical experience for those who learn, earn, and then give back.

By Ben McDougal, ago

Bookmarks

Anticipation, fear, and excitement. These are healthy sensations that emerge as we create bookmarks in life by experiencing new things.

It’s easy to forgot for those who often look forward, but we are blessed by many renewing moments throughout life. The start of a new day, first dates, holidays, weddings, vacations, the arrival of a child, birthdays, the first day of school, a new job, the launch of your own company, and perhaps when you fully accept that we may only have one life to live.

This reflection on fresh beginnings and how we’re invited to create bookmarks in life spawned as I embark on my expanded role with Techstars. As a tech founder and entrepreneurial ecosystem builder, Techstars is an iconic organization I’ve always admired. They support entrepreneurs with education, resources, and mentoring that is exponentially compounded by a global network. What started as exploratory ecosystem building, quickly transcended into a more involved role with the Techstars Iowa Accelerator.

I’m grateful for this opportunity to be the entrepreneur in residence focused on ecosystem development. As you hear me often say, the energy of accelerating others is unmatched. Supporting more inspired founders while connecting a community of remarkable mentors is such a gift and yet another bookmark I’ll always appreciate.

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Visualizing your career portfolio as a dynamic pie chart is something I write about in YDNTB. Along with this healthy exercise to reflect on your own personal bandwidth, having this graphic on your phone adds a quick reference for introductory conversations as well. Here’s a peek at my current career portfolio.

As you marinate on your own state of now, be thankful for the bookmarks in life that you’ve established by exploring something new. Think about what you started and how’s it’s evolved. Remember everything can change so if it’s time to create a new bookmark in life, avoid the natural temptation to wait.

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Someday is dangerous. Today is all you have. Start.

By Ben McDougal, ago