Startup Weekend

Live Event Management

There’s something exhilarating about bringing people together to enjoy an experience you built. Anyone can bring a few friends together. Creating an environment for the public to connect requires more attention.

Controlling the chaos of an event is easier with solid planning beforehand. First-time events are always the hardest, but every event has unknowns. The more thought put in before people arrive, the smoother your attendees’ experience will be.

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I’ve developed and managed countless events throughout North America. More tips and tactics, as well as, insight from my own experience is layered into the Event Management section of YDNTB.

Basic details include the venue, time, and guest list. Who’s the audience? Based on those you want to attend, how can the venue support the right vibe and is it accessible? How will transportation and parking work? Looking at community calendars, will your event compete with other related events?

With basic event details in place, how can you promote this event so people you want to attend notice it? Will a website be needed or is social media enough? Is it free to attend or will there be a cost? If it’s free, how will you cover costs? Speaking of costs, how could sponsorships work? What’s the plan for food and drinks? Is there a registration process? If not, will you still be able to gather attendee data? Is security staff needed?

Think about your own goals for the event and how you want attendees to feel when they leave. Beyond the basics, what’s the agenda look like? Will there be any sort of programming? What about special speakers? As the host, if you plan to say a few words, what are the key points you want to make? Are activities planned or is casual conversation enough to keep everyone engaged? Will you be able to capture enough media while still managing the event? If not, does it make sense to hire someone to capture photos and video to use later? Can you rally attendees by connecting them on social media before, during, and after the event? Could showcasing live social media activity boost awareness for those unable to attend? Where’s a good place to send everyone interested in the after-party?

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Stay tuned! Next week we’ll shift focus to online events.

One common mistake is assuming an event is over when the last guest has left. Detailed planning leads to smooth events. Concerted efforts to commemorate events lead to future opportunities. Finish strong with thank-you notes, tagged photos, video highlights, recap articles, and follow-up conversations.

Event management is challenging and stressful, but super energizing. The more you bring people together, the more effective you’ll become. As the basics become second nature, it’s easier to get more creative. This leads to larger crowds, more memorable experiences, and longer-lasting engagement. Like everything, the more you practice, the better you get.

By Ben McDougal, ago

Ship It

We are all artists. No matter what you create, there’s a distinction between creating art and shipping it.

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Here’s a useful definition of art. How does (re)defining art this way change the way you think about your own contributions? What is your art?

My favorite author, Seth Godin, often writes about going beyond the status quo by creating remarkable art. As we explore and expand our creative practice, Godin also suggests that if we don’t ship our art (i.e. send it out into the world), that it is all for naught. He leans on how art is all is about connection, and if nothing is shipped, there cannot be connection.

Entrepreneurs, intrapreneurs, side hustlers, students, and community builders willing to ship, fuel positive change with their art. Unfortunately, the ego often fears external evaluation. This fear is compounded when a lack of success may occur, which is always possible. As apprehension calcifies over time, it becomes tough to resit the temptation of hiding our thoughts, emotions, and activities within the safety of solitude.

Creating art to enjoy by yourself can build skills and provides internal layers of sentimental value, but to go beyond the status quo, push past the fear of feedback.

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Failure is an illusion. We either succeed or learn.

The world is loud, so avoid wasting time shouting just to make noise, but know that we need you to ship your art. This encouragement is not an excuse to rush into bad ideas, ship something that hasn’t received proper attention, or not deliver on a promise. It is however, a friendly reminder that pursuing perfection can devolve into an enemy of progress.

We’ve all heard inspiration like that before, but listen to those you admire. Perfection is rarely required when all you need is enough success to continue creating art. Let such liberation fuel confidence. Translate expanding confidence into fresh curiosity. Augment this curiosity with creative action. Rinse and repeat.

As belief in oneself grows, one interesting hesitation is disguised by good intention. We tell ourselves it’s not wise to be too self-serving. This is virtuous, but sometimes endless humility makes silence feel safe. As we protect ourselves by staying quiet, a self-limiting restraint develops. For example, many people find writing into journal to be therapeutic, but are quick to dismiss the idea of sharing these beautifully raw writings with others. Of course it’s good to internalize some things, but as you learn more about yourself through writing, know your art can make an expanded impact when it ships.

Ready to ship your art? Think about your own super powers and the people you care about. How might connecting these two things provide value? Experiment with small actions and as this develops into a practice, expand the connected nature of your creativity. As your art connects with those who care, find a cadence that allows you to be consistent. Seth Godin suggests that we all ship something daily, but one size does not fit all and the right tempo depends on the art you’re planning to ship. To find your own signal, consider your personal bandwidth and the audience you seek to serve. Talk with others and experiment, then tweak your timing to find the right rhythm.

If you’re shipping art, I’d love to hear what makes it remarkable and how you stay consistent. If you’re looking for new ways to make a ruckus, the Roasted Reflections library and my curated Resources page will help spark fresh movement.

No matter your current state of now, thank you for continuing to create art. More important, thank you for being courageous enough to ship it.

By Ben McDougal, ago

Early Moves

So you have a business idea you’d like to explore? Yes!

It’s easy to say “Let’s gooo!” but when you say yes to something, you’re also saying no to something else. This is opportunity cost, so be strategic with your early moves. Before you go too far, remember that an appropriate “no” early on is better than a long, wrong “yes.” Let’s explore how to decide what ideas to activate and how to help them bloom.

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Things you dedicate time to will grow.

It takes discipline, but time alone with any idea is a good way to avoid swinging at bad pitches. Dig into online research before going too far. Determine what related products or services already exist. Run some numbers. Talk to potential customers and see if you can snag a few preorders. The goal is to understand the realistic impact you may be able to make in the market by confirming it’s something strangers are willing to pay for.

If you start to feel genuine interest, talk with others who may be interested in collaborating. Think about your own skills to identify where you’ll need help. Attend related events to further qualify early concepts. Even if you’re not ready to share details, the readiness to Show Up and #GiveFirst often leads to new allies who can connect dots as you continue working through ideation, team development, research, and testing.

Before you go much further, take a pit stop with your future self. Is this a business/market you want to work on for the foreseeable future? If you like to quilt, it doesn’t mean you should start a quilting business. The hardships that come with being a business owner can actually kill your passion. Dance with all your ideas, but recognize when something should remain a hobby.

Early moves are exhilarating, but there’s value in being efficient as you decide if something is going to work. If this evolving business idea continues to touch your heart after internal and external analysis, you may have something ready to pursue! Inspiration is perishable, so when this happens, be ready to take action. As you do, stay patient. It’s not how fast you move, it’s that you find ways to keep moving. Avoid the headline trap and find lasting energy knowing that even hints of progress can nurture an idea toward reality.

As you continue moving forward, think big, but remain realistic by doing one thing really well. Stay intellectually humble and welcome doubt by working with others and be ready to iterate quickly. It often takes many versions of an idea to land on something ready for the wild.

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

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