Roasted Reflections

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

Show Up

Surrounding yourself with fellow students, entrepreneurs, and intrapreneurs will keep you motivated. The goal is to find a balanced collection of community events. Commit to those who complement your life while seeking out new groups that make you nervous. This combination will connect you with people who can support, but also expand, your world.

Once you lock in on a few groups that can push you to be your best, show up. It sounds easy, but consistently showing up takes dedication. When we commit to showing up, we are being generous with our time, and generosity leads to trust. As trust surges, more meaningful interactions occur. This will increase the value you give and get from the community, which makes it easier to show up.

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Whether it’s a tribe you trust or a brand new experience, don’t waste your time by attending an event just to say you were there.

When you arrive, say hello to everyone you know. After catching up, shift the focus to meeting new people. For a jump-start, ask a friend to introduce you to someone you don’t know. If that’s not an option, go mix it up alone.

Be bold enough to enter existing conversations without an invitation. One way to do this in style is find a small group of people talking. Wait until you’re noticed, then casually say, “Hey, folks, whatcha chattin’ about?” Be respectful and prepare to expand on whatever they’re talking about. The group will soon want to know why you decided to join their conversation. It’s tempting to use this moment to talk about yourself.

Instead, surprise them by not trying to take over the conversation. Ask a question or share an intriguing thought that relates to the current discussion. The objective is to deflect the focus back toward the group. This deflection will weave you into the fabric of the discussion. You’ve now become a part of the group’s conversation. This will provide a chance to share your story with a more natural flow. Even as you explain your work, remind yourself that everyone loves talking about themselves. By letting them do so, you’ll be less as an intruder and more of interested addition to any discussion.

Perhaps you’re in a group and someone decides to join you? Be quick to expand the circle and compliment their initiative. Get curious and allow your inclusive vibe to create yet another new connection.

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Saying “yes” leads to more adventure, as the universe rewards our ambition.

By Ben McDougal, ago

#1 DAD

Little startups that pay in love are a blank canvas that comes to life through you.

By nature, parents want to provide the means for children to go beyond their potential. As entrepreneurs, when we see the best of ourselves in someone we care so much about, a sense of renewed purpose often emerges. To celebrate Father’s Day, here are a three parenting tactics I’ve found especially interesting.

You’ve Got Mail

Secure an email for your little one, then use this communication channel to write to them as they grow up. Whether you start writing before they are born or begin this practice later in their life, imagine what a gift an inbox full of thoughtful updates will be in the future! This new email can be shared with family and used for future account setup if you want, but at a minimum, you will have created a personalized time machine.

Along with all the sentimental content you’ll deliver someday, your kids will appreciate having a solid address to use as their primary email someday. Such a preferred email address may not be available years from now, so I’d suggest securing something they can use long after childhood. For example, [email protected] is a safe place to start and while you’re at it? Perhaps it’s a good time to register a domain in case they ever want to build on their name.com.

They Grow Up

Similar to how death can inspire us to live, recognizing that kids will grow up, reminds us to enjoy everything about each 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 tell family stories in a way that makes memories easier and more fun to revisit. Most people have an endless collection of photos/video on their smartphone, but scrolling around a digital device doesn’t translate into something a group can enjoy together. As we all know, it’s easy for good things to get lost when there’s so much noise as well.

Your future self will thank you when you spend the extra effort to organize content outside of the latest social media platform. This attentive, pro-active organization will also make relics easier to craft. Whether it’s a photo slideshow you put together each year, a fun collection of audio recordings, something printed that sits on the shelf, or a video edit that highlights your adventures, the time spent compiling these legacy projects will rarely feel wasted.

Avoid Routine

“Time flies” and “they grow up so fast” is accurate, but I’m convinced that avoiding routine may slow down time. The freedom to be spontaneous is a privilege and everyone will define such freedom differently, but a proven path to explore such a reality is entrepreneurship. Boundless hard work, dedication, and resiliency are what it takes, but our own suffering provides a stronger sense of purpose and the chance to enjoy more treasured time doing things that make us happy.

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

The time and energy family life requires is immeasurable, but as the love from your kids somehow unlocks more hours in the day, new perspectives form and fresh motivation is released. 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