Roasted Reflections

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

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

Startups that pay in love are a blank
canvas that comes to life through us.

By nature, parents want to provide the means for children to go beyond their potential. Family requires immeasurable resources, but the love from our kids unlocks more hours in the day. The added productivity comes from seeing the best of ourselves in someone we care so much about. Purpose is renewed and the heart we put into our creative work can make our presence as parents even more interesting.

Summon Stories

Children grow up fast, so we stay in the 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 summon family stories.

Every moment is special. As creation becomes second nature, handpicked memories can be stitched together to revisit interactively, any time, with or without you.

Most of us have an endless collection of photos and video on our smartphone, but scrolling around on a digital device doesn’t translate into something a group can enjoy together. It’s easy for good things to get lost in so much noise and spoken storytelling is always merry too, but why not paint more stories with a few added brushes?

Quiet relics like photo slideshows, something printed that sits beautifully on the shelf, a mix of audio recordings, art on the wall, or a cinematic feature film that highlights your adventures. You’re the creator with endless ways to create.

We all do a form of this, because family is our favorite, but the time required is real. A rigid cadence is not required, since any day is a good day to ship this type of of art. In the early days of photos and video, it was only birthdays and Christmas — now everyday is a holiday. No need to rush, but keep producing new surprises. Everyone will love the end result and as more come together, the growing playlist becomes a sequence of stories that follow kids growing up. With our constant collection of content, a good story is always ready to tell, but at a minimum, why not share an annual gift with your kids, partner, and other loved ones?

Along the way, attentive and controlled organization will make a growing collection of relics easier to craft. This takes an ongoing commitment, but file management is easy and helps bring life to life with shared memories.

Your future self will then thank you for an effort to organize this heartfelt content. Share in public if you want, but that can alter the art if it becomes a show. Do it for yourself and your favorite people first. Organize what will be a massive library offline, then, if you want play with the transitory channels of social media, that’s a personal choice.

No matter who resists whatever it may be, time compiling legacy projects will rarely feel wasted. It’s using our real skills to commemorate those we love. Scanned memories may give us content without capturing it in the future. For now, it’s up to us to trap time for personal storytelling.

Compensation is not money, but this does enhance your content creation skills for other areas in life. Technology also makes editing content more productive, but this is not your average task. This is the type of sincere storytelling you enjoy spending time with.

As kids grow up, these projects will have the lowest view counts, but always be your very favorite. Looking ahead, it’s crazy to imagine being a child right now, then receiving such a gift from my parents someday!

You’ve Got Mail

Consider setting up an email for your little one. This inbox can be used as a communication channel to write to your child as they grow up. Whether you start writing before they are born or later in their life, imagine what a gift this inbox will be in the future! This email address can be shared with family and used for online accounts if you want, but at a minimum, this curates a personalized time machine full of thoughtful updates.

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

Along with sentimental content, your kids will appreciate an email address that can be used after childhood. First and last name with your preferred email provider should stand the test of time. This is also a good chance to register a URL using their first and last name. This can connect to their email or support a personal website someday.

Avoid Routine

“Time flies” and “they grow up so fast” is accurate, but avoiding routine may slow down time.

The freedom to be spontaneous is a privilege and everyone will define such flexibility differently, but a proven path to explore such a reality is entrepreneurship. Boundless hard work, dedication, and resiliency are what this lifestyle takes, but suffering provides a stronger sense of purpose.

As this purpose is layered in later stages of life, experiential wisdom can be channeled into more treasured time doing things that make us happy. While hardship is part of the deal, children make their parents happy. 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