Entrepreneurship

Love Letters

“Dedicated to my co-founder in life and our startup that pays in love.”

Cheers to the love of our lives. This opening dedication in You Don’t Need This Book: Entrepreneurship in the Connected Era is fixed on the fact that significant others are elemental to an entrepreneurial lifestyle.

When so much is poured into something we care about, it brings everyone along for the ride. This makes success fun to share, but when dips emerge, tension will test the best of us. Many families build love triangles, but partners building in completely different realms is just as familiar. Loved ones may not understand all that’s surging through each other’s ambitious adventure, but when trust is minted, healthy individuality allows each person to achieve more through a shared appetite for risk.

A < H

To visualize how trust creates exponential opportunity, put your hands together. First, make an “A”. Each hand represents one partner. When relationships are built in the shape of an A, the constant contact actually becomes a limitation. The centering line of trust is established, but the top point limits how far each line can be extended.

Now, use your hands and make an “H”. The center line of trust remains, but there’s now space for individuality. Each of the two horizontal lines can continue to grow beyond what would have been possible alone. Individuality can feel apathetic, but when two people trust each other enough to build their own neon future, a brilliant fabric is set free to shine. This fabric can also become unbreakable, as threads of purpose are woven together with everlasting love.

Risk Appetite

Even with loving individuality sustained by trust, a shared appetite for risk still correlates through the environment, engaged networks, and what our partners provide. The quiet truth is that if there’s a singular source of income, stability is paramount. If there are multiple sources of income, there can be more comfort in the unknowns that come with building something new. Our current situation will always present limitations, but can we produce when others consume? Will we continue shifting gears to keep building without a map?

If such a calling brings you to life, what can we do to increase a shared appetite for risk? If work/life balance is an illusion reserved for the status quo, perhaps peace awaits those who encourage the latest creative season pf their forever friend. Setting an example of unselfish support can translate into positive momentum that benefits our partners, while also adding fresh space for our own exploration. The loving leash is lengthened as each partner delivers on promises (or quit the right things, at the right time) and the strengthened trust brews more freedom to flex.

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I am nothing without the love we share.

Before we ink this tribute to those who support us, let’s play with a paradox. Does everyone have an entrepreneurial spirit? It’s easy to say yes, but my favorite response considers the trust-based privilege of inviting strategic risk. In short, we may all have a creative spirit. When an appetite for risk is applied, the innovative spirit gets stirred into a delicious recipe that can be tasted with endless variety. It’s students tinkering with no permission required. It’s indispensable intrapreneurs fueling positive change in existing companies. It’s the side hustles that evolve a leader’s diversified career portfolio and the founders willing to solve problems with pain-killing solutions. While lone wolves build capacity to explore their own uncertainties, exponential opportunity await the team that builds with a shared vision.

Humans seek purpose, peace, and happiness. The family we choose influences our own path toward career nirvana. Be kind to yourself by choosing a partner wisely, then be your best knowing that when the credits roll on a life well-lived, our loved ones will be first, last, and all that’s in between.

By Ben McDougal, ago

Executionist

Nobody cares about your great ideas.
They care how we make ideas happen.

This tribute to action was originally titled execution, but that’s insufficient. To honor such ingenuity, let’s loudly celebrate those who apply action to nudge the world, by calling them executionists.

Executionists appreciate planning, but don’t get stuck in endless brainstorms. They’re not rushing into bad ideas, but they are often the first to tinker. Action-based execution is why the title of my book (and podcast) will remain true. It even grounds the preface of You Don’t Need This Book, which I thought might be neat to highlight here:

There are good reasons why we have so many clichés about talk being cheap. Action is required when it’s time to get things done. Cheers to so many who don’t stop at ideas. Heretics who build when others don’t. Leaders who choose to make a ruckus without permission and in doing so, go beyond the status quo by evolving ideas into reality.

Executionists keep the promise.
Executionists leverage uncertainty.
Executionists perpetually learn by doing.
Executionists connect dots with real skills.
Executionists courageously communicate.
Executionists take time to be detailed oriented.
Executionists stay organized to be efficient.
Executionists add pieces to the puzzle.
Executionists enjoy shifting gears.
Executionists are Serendipitists.

Extra Shot
After three years, decisions were made to spin away from the weekly cadence of my writings. Fresh episodes of YDNTP will continue brewing innovative energy each week and occasional contributions may still land into Roasted Reflections, but these last few writings of 2023 are a closing finale.

By Ben McDougal, ago

Triangulation

Cross-checking helps determine distance, maneuver around obstacles, and identify missing objects. Alongside the math, a triangulated team diversifies real skills and increases dependability.

With more distinct perspectives, entrepreneurs add synergy that accelerates forward movement and increases confidence when the same problem is attacked from multiple angles. This nimbleness can be leveraged as co-founders also create an invigorating culture that makes each person feel significant. With back-to-back episodes of You Don’t Need This Podcast featuring my two co-founders in FliteBrite, what a wonderful chance to reflect on talented friends who build as one.

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“One’s company, two’s a crowd,
and three’s a party.” -Andy Warhol

If you’re on the prowl for co-founders, consider the value of triangular patterns. Connectors become connected, so show up and be quick to make interesting introductions. Even when the first degree of contact lacks obvious opportunity, remember it’s often the second and third degree of connectivity that delivers more precision. Over time, generosity within an entrepreneurial ecosystem will expand and tighten engaged networks. Instead of forcefully recruiting co-founders, the open-ended activity of a serendipitist will have us colliding with friends we simply haven’t met yet.

When it’s time to build, bonds that formed naturally will support lasting collaboration with people you already respect. That said, established trust is not an excuse to get complacent. From start to finish, be honest and transparent. Every story ends, so invite difficult discussions early and often. Agree on terms, leave space for change, structure the business, maintain an operating agreement to ensure clarity with less tension, and lead by nurturing the power of triangulation.

  • commit to abundant communication
  • invite responsibility, keep the promise
  • remain attentive to details
  • take blame, give credit
  • celebrate in style

Lone wolves can move mountains and rare resources are required with more human capital brewed in, but the expanded capacity and ongoing resilience makes this odyssey worthwhile. When long-term players play long-term games together, the chemical reaction is an affinity toward work that feels like play. Cheers!

By Ben McDougal, ago

Echos

The echo of an idea is always fading.

How can we extend ideation long enough to activate early moves, blow through barriers, and maintain lasting enrollment? This is clearly a loaded question. Much goes into enabling ideas into reality and the rate of an idea’s degradation depends on a million factors, but let’s sip on the artistry of pushing without being pushy.

As seen in the Ideation and Research chapters of YDNTB, personal reflection is the easiest way to think through the various angles that might make an idea interesting. This private contemplation doesn’t require much skill and we don’t get stuck trying to earn the attention of others. Unfortunately, the ease of your own activity is matched by the hardships that await those who don’t let ideas breathe. This is why stealth mode is precarious and ongoing customer discovery is key.

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Will you spend time or money?

When we share a new idea with someone else, the situation becomes complex. This is the moment we put our idea on a hook. It’s when we push past fear and invite doubt. Connecting dots within such complexity is difficult, takes time, and is never straightforward. Research helps to build confidence and adds clarity to how opportunities are articulated. While this preparation helps guide others through layers of understanding faster, a blend between patience and urgency is required to align interest.

This makes blunt repetition tempting, but ineffective. Whether it’s potential co-founders, mentors, early adopters, or investors, more of the same (without execution) can chase away interest. To avoid potential fading too fast, find different ways to motivate movement.

For a fun visualization, let’s imagine a small pond. If one pebble drops in, the lonely ripple would be obvious, but also fades fast. While it made a splash, it’s soon forgotten. Now, imagine many pebbles being thrown in different ways, all around the pond, and over time. The pond is now alive! The echo of each pebble is magnified and the abundance of rippled collisions leave a more lasting impact.

Like this pond full of pebbles, we can nudge progress long enough to activate action by adding variety into how we introduce and continue to explore an idea. Conversation in different environments, creative analogies, inquisitive questioning, active listening, talking about anything else, releasing reluctance, or getting more people involved are all ways you can keep building without seeming frantic, repetitive, or desperate. This intentional diversity allows different echos of one idea to each feel different, and yet, all bounce in the same direction.

By Ben McDougal, ago

Small Business Owners

Words matter. When “small business” and “small business owner” is used over and over again, it begins to feel belittling. Together, opportunity awaits those who brew fresh ways to talk with and about small businesses!

First, let’s get an elephant in the room. Everyone understands the need for business categorization within an economy and yes, size is a simple metric. Entrepreneur Support Organizations (ESOs) are quick to explain that because of government policies, regulated programs, and the history of small business owners not thinking of themselves as entrepreneurs, using “small business” has become second nature.

The opportunity exists within events where the assemblage are small business owners, but what about this fear of marketing that won’t resonate without a clear call to “small business owners”? Here’s the trick. Use small business terms to gather awareness, but then let those technical terms chill once everyone comes together. This ensures clarity in branding, online activity, and event promotions. As events get underway, emcees, speakers, panelists, and staff can embolden the audience by using “small business owners” as necessary, but intentionally use more alternative titles that add depth to the narrative. Instead of everything being stuck on small, try these seven synonyms that describe greatness, importance, appreciation, growth, and yes, small business owners.

  • Entrepreneurs
  • Leaders
  • Students
  • Innovators
  • Heretics
  • Creators
  • Community Builders

As people who may have only identified as a small business owners start using enlivened vocabulary, these side conversations become a signal of something lasting! If this effort continues at future events, more people will connect with more terms they feel inspired by. This exposes small business owners to even more relevant resources, helpful ideas, and different areas to confidently explore within an expanding entrepreneurial ecosystem.

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When was the last time you wanted something important to be small?

Using this working draft of synonyms, we can each quietly inspire more inclusivity through fresh assimilation at events. Even if policies remain rigid, more people will learn to celebrate and identify with more codifications.

Over time, more will feel allyship with all that is entrepreneurship. We will remain proud small business owners, but just as vested when we hear whatever the latest jargon may be.

By Ben McDougal, ago