Intrapreneurship

Uncharted

Building without a map is a bold art form.
It’s challenging, dangerous, and rewarding.

It’s challenging, because these expeditions call for initiative to show up, but also an unknown amount of resources to stay persistent. All seven capitals (intellectual, human, financial, institutional, physical, network, and cultural) can be hard to find. Celebrating what we have with a sense of abundance, attracts more of what we want. As different types of capital connect, staying balanced with your personal bandwidth requires attention, but when we care enough and remain realistic, we give ourselves the permission to keep building.

Uncharted crusades can also be dangerous. This probably won’t go as planned and opportunity cost is high with endless ways to spend our time. Even when the odds are against us, a healthy obsession paired with a willingness to succeed or learn cultivates a potent mix of curiosity, optimism, and righteous recklessness. Those willing to try have a huge advantage over everyone else willing to wait.

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What might you regret not doing?

When exploring the unknown for the first time, be clever, collaborative, and patient. Also, remember that winners quit all the time. They simply quit the right things at the right time, so get passionate without falling in love with impossible. To do so, ask for help. There’s much to learn from heroes, mentors, and those you seek to serve. Success and failure leaves clues, so speed up progress and avoid pitfalls by leaning into the tribes you trust.

When you’ve built without a map for a long time, the highs and lows strengthen decision making, while also making the unknown less intimidating. Experienced way finders gather feedback faster, measure the right metrics, and appreciate the hardships without allowing pride from the past to be misleading.

We know how rewarding it can be to build an event, business, or relationship you’re proud of. To dance toward the unknown, be thoughtful with early moves, but don’t get paralyzed by perfection. Sustain growth with sequenced storytelling. Be urgent, but not frantic by activating trust channels that stimulate accountability. Welcome feedback like a scientist, listen with concentration, and savor metrics beyond the money.

By Ben McDougal, ago

Captive

I was catching a quick nap on a recent flight.

All the sudden, our flight attendant broke the peaceful silence. Not to share a friendly update for passengers, but to rattle off a forced sales pitch for their branded credit card. Ouch.

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Attention is hard to earn.
If you have it, don’t waste it.

Now, let’s imagine an alternate scenario. Instead of an unwanted interruption followed by an impersonal script that makes most think less of the brand treating us like prisoners instead of customers, what if the same offer felt more like a gift? Like a special surprise? Something that makes you feel appreciated!

For example, how would you feel if you were told that you were selected to receive a free adult beverage or tasty snack, paired with the exact same credit card application?

Whether you decided to apply or not, the complementary surprise was just to say thanks for being a valued customer! This personalized presentation would naturally snag the attention of nearby passengers. As word of mouth amplifies interest, similar offers could be made for those willing to complete a credit card application.

That’s just a thought exercise, but we’ve all sat in situations where we were part of a captive audience. Whether by choice or not, there’s a fine line and a big difference between an experience that adds or detracts from an experience after the sale.

How do you treat your existing customers? Do they only get attention when there’s issues or you have more to sell? Perhaps there’s untapped creativity that could inspire more lasting joy by letting go?

To spark fresh creativity, consider a quest to delight customers in unexpected ways. Giveaways (without obligation) are an easy way to see how existing customers may react. Impromptu phone calls, handwritten notes, and basically any gesture that shows you care, will naturally retains better customers as well.

As this thoughtfulness is felt within your customer’s experience, more true fans will stick with your team because they care as much as you do. This translates into customer retention, because true fans take pride in staying connected. They have more patience when issues arise and get excited to share your charming work with others.

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“Once you wow an audience, the same trick may not work anymore.” -Seth Godin, Free Prize Inside

By Ben McDougal, ago

Not to Lose

I’ve been around soccer the majority of my life.

Whether it was traveling with the college team my dad coached as a kid, playing club soccer at an early age, focusing on the sport in high school, playing all through college, or being the product of my first entrepreneurial venture, soccer was a part of my identity for over 20 years. This team sport helped me push to be my best, but the sense of belonging is what made it special.

As I’ve enjoyed the World Cup in Qatar, I’m reminded how easy it can be to get ahead in a match, before slipping into a dangerous trap. Instead of staying sharp by maintaining the offensive pressure that earned an early lead, it’s tempting to start playing not to lose.

In soccer, this often means a team sinks back into an overly defensive formation. Less variety invites frantic desperation and the added pressure often leads to an equalizing goal being scored by the opposing squad. Even if the need for another goal shifts your team back into a more balanced attack, the momentum has shifted.

When applied to business, getting ahead and then playing not to lose can be seen all over the map. For instance, snagging a few early adopters, then assuming customer discovery is over. Hiring new talent, then hoping everyone can work together without initiative. Launching a new product with existing customers, then not supporting them through the chasm of change. Securing product-market fit, then avoiding innovation due to a misguided sense of risk. Finding generous mentors, then forgetting to nurture relationships. Those are just a few, but many leaders are lulled into this trap that’s defined by a sense of scarcity.

Tactics to stay ahead differ based on situational factors, but when in doubt, trust that uncertainty is certain. Be strategic to avoid recklessness, then stay on the offensive by leaning into the pain. As you find fresh ways to serve customers, continue celebrating milestones and stay ahead with initiative to keep building beyond the fear of losing.

By Ben McDougal, ago

Tenured

Recognize, connect, and support those who consistently delight those they serve over a prolonged period of time. Rewarding such an initiative makes sense, but at what point does the comfort of a rewarded role devolve into a willingness to sail into the sunset?

When starters run into the aloof, misaligned energy can lead to a standoff. Time is the ultimate release, but what if progress is needed now? Every situation is different because of the complexity of an environment and the people/organizations involved, but here are tactics that seem to work no matter the circumstance.

The first uses social currency. It requires a change maker to set their ego aside, and instead, celebrate all that’s been achieved by the accomplished, yet tired gatekeeper. Use respect, kindness, and appreciation to form a bond. Relationships that feel less transactional often create leniency toward new ideas. When a crack in the wall of inactivity is created, be glue that maintains the integrity of the existing system. For example, “I’m too busy” is a common qualm, so lean into that pain by offering to execute on the idea that has sparked mutual interest. It’s important to be realistic in these moments, because when promises are made, credibility is on the line. As you not only light a path toward progress, but also champion change by evolving ideas into reality, trust is gained and your ability to continue making a ruckus increases. Want to extend your leash further? Take responsibility for failures, but give all the credit away when success is achieved.

If a larger organization is involved, another interesting tactic invites the tenured leader to level up the team by activating a colleague. This provides a new hire the chance to get involved within the entrepreneurial ecosystem, while the organization is seen as engaged within their community. It’s hard for some to understand that time spent in the wild is often more valuable than clocking time in the office, but if the organization allows this person to show up without limitation, everyone wins. The new community member feels the innovative energy and brings more intrapreneurial vibes into the organization, while the community benefits by having another trusted organization in the mix.

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“The way we make things better is by caring enough about those we serve to imagine the story that they need to hear.” -Seth Godin

If you’re reading this, you may be tenured, but it’s unlikely you’re tired. That said, we’ve all found ourselves in a motivational rut or lacking a clear sense of purpose. Along with a few solid sleeps, when I feel the urge to settle, it helps to have fun, build into other areas of your career portfolio, take a few days to rest if necessary, and then get back into the startup community. This creates opportunities to #GiveFirst, ask for help, or get extra curious about the creative work of others. Soon you’ll find new opportunities to collaborate.

New connections that emerge can bring you out of the motivational rut. They can boost your care meter and will add fresh personality to your work. Along with sparking fresh direction(s), you’ll be motivated by others and soon find new ways to be generous with your art. If you’re still thirsty for motivation after tapping into the entrepreneurial ecosystem, I’m here for you as well. Together, we can refuel the idea machine to avoid wasting any more time with being tenured, but tired. Sleep when you’re dead, my friends. Let’s keep building.

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“There will come a time when you believe everything is finished. That will be the beginning.” -Louis L’Amour

By Ben McDougal, ago

Bloop

Imagine yourself as a circle.

It’s tempting to suggest a sphere, but the added dimension is not necessary for this metaphor. Alright, with your circular self, take a tiny portion of the arc and “bloop”… push it beyond the circle’s circumference. Even the smallest nudge gives the entire circle space to expand.

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I had fun making all sorts of sounds as I considered the title for this reflection, but I’d love to hear how you’d describe the sound of such an expansion. Also, since I had to look up the terms to ensure this metaphor was translated correctly, here are the parts of a circle.

There’s plenty of research behind the idea of small improvements adding up. As we hear from inspired speakers and read about in Atomic Habits by James Clear, if you get one percent better each day, you’ll end up thirty-seven times better by the end of a year. It’s hard to define “better” and such steady progress would surely require sacrifice, but most will agree that small choices don’t make much of a difference, until they add up.

While establishing systems that support good habits and compiled improvements are great, this reflection is more about welcoming singular moments of exploration and growth, even when it seems unrelated, weird, or insignificant.

Perhaps it’s trying something new without preconceptions, saying yes when no is status quo, or being the initiator when movement is seen as risk? As we poke the box and invite a bit more bloop in our life, we give ourselves an opportunity to grow as our own circles expand.

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To thank those who have enjoyed brewing on these Roasted Reflections every week for almost two years AND to say hello to some new friends, here’s a free gift just for fun!

By Ben McDougal, ago