Entrepreneurship

Stand Out

Being remarkable in a networking environment is not rocket science. Be friendly, vulnerable, funny, curious, and eager to help without getting stuck in one place.

As you continue to show up, you’ll learn from others and also learn more about yourself. You’ll be able to ask great questions and be adaptable to any conversation. You’ll need to share your work less, which will allow you to make more introductions. This will make you stand out as a connector.

Ready to shake things up? Avoid the temptation to ask the most common question at networking events: “So, what do you do?” Instead, consider more interesting ways to get people talking.

– How are you feeling?
– How do you like to spend your time?
– What does a day inside your office involve?
– What mindset inspires your best work?
– What’s a recent project you enjoyed working on?
– Are there any roadblocks you’re working through?
– Is there anything I can help you with right now?
– Would you do this work if money weren’t a factor?
– What did you do before your current role?

You only have a moment to make a good impression. It never hurts to throw in a specific topic to help people remember you. Avoid small talk like the weather. Also, family means everything to most people, but avoid going too far down that rabbit hole. Here are a few creative conversation starters to sprinkle in.

– What are your superpowers?
– Where did you travel to last?
– Have you ever been a mentor or an advisor?
– What are you reading or listening to right now?
– How would you describe the internet to a child?
– If you’re a pro wrestler, what’s your entrance song?
– Is there anything that may surprise me about you?
– What’s an interesting paradox you‘ve answered?
– How do you define success? How about happiness?
– Have you ever regretted not doing something?

When it’s time to move on, there is also an art to exiting a conversation. This is handy when conversations have gone on too long. One tactic is to bring more people into the conversation. Kindly introduce everyone to each other. You then have the option to stick around or excuse yourself. Even if you leave the chat, your energy will remain a part of that new conversation as you mingle elsewhere. If you’re at a networking event, another approach is to joke that it’s time for both of you to go meet more new people. This lighthearted suggestion eliminates any awkwardness.

If you’re the one holding conversations too long, you’ll know it when people try similar exiting tactics on you. To improve your relationship-building skills, stop draining the energy from each interaction. Be cognizant of how long you hold onto each conversation. Abandon the idea that everything must happen in one exchange. Even if it feels abrupt, don’t be afraid to move away from conversations before they feel complete. Ending interactions a bit early leaves room for more conversation next time. This creates a subconscious gap to fill and therefore more reasons to reconnect.

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

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

Weekend Sprint

We just wrapped up Startup Weekend Iowa.

This was an online event, so our organizing team compressed what is normally a 54-hour, localized, in-person hackathon… into just 26 hours of people talking, typing, working and connecting together without the barrier of location.

Thanks to our own Wizard of Oz, virtual interactions were seamless and I was set free to creatively facilitate this high stress, no risk experience. It was energizing to have 25 participants and 15 mentors connecting to build two companies that pitched head-to-head for esteemed judges on demo day. This was a statewide event for Iowa, but the international element was in full effect as we also had new friends teleporting in from Canada and India to participate. While most of the event was hosted in a private platform that we called “the venue”, here’s a YouTube link to “the stage” where our keynote kickoffs and demo day were live streamed.

These weekly reflections, which I’ve been calling Roasted Reflections, are purposely timeless, but I share this brief event recap because it reminds me how easy it is to build when only a few people decide to work together. Yes, in-person gatherings create more random, serendipitous interactions, but I continue to marvel at how new interactions can be so efficiently ignited through these online interactions.

This was actually my first Startup Weekend experience! In the past, I convinced myself that my career portfolio was too full to build yet another new company. The infrequency of a local event and the anticipated time required were also factors in my past decisions, but now I realize, this combination of considerations led to a misguided assumption.

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You hear this tweetable thought often, but smart people change their minds all the time.

Startup Weekend can be a place where participants come together to build a business idea into reality, but it can also be a wonderful chance to catch up with friends, learn a new trick, mentor people exploring their own entrepreneurial spirit and/or simply observe some magic in action.

As one of the organizers and lead facilitators, I enjoyed a front row seat that allowed me to commentate the weekend while helping two teams build ideas into reality.

The energy of this weekend sprint was remarkable, but I noticed something as we all sat back and virtually celebrated demo day over a few brews during afties. It felt like the last day of summer camp. Everyone had been working alongside each other and while closing things down felt bittersweet, you could tell everyone appreciated the opportunity. This group had done something they were proud of and there seemed to be an unspoken premonition that Startup Weekend was not the last time these starters, makers, doers, and dreamers would come together to collaborate.

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Building alone is easy. Find friends to make it fun.

By Ben McDougal, ago