Entrepreneurial Ecosystems

Small Business Owners

Words matter. When “small business” and “small business owner” are overused, it becomes belittling. Breakthroughs await those with expanded vocabulary.

First, let’s get an elephant in the room. There is a need for categorization between different types of businesses, and size is an obvious differentiator. This determines how government policies, regulated programs, and other environmental resources are distributed.

Unfortunately, broad categorization leads to business owners not thinking of themselves as entrepreneurs.

Whether it’s the size of a company, revenue, or other quantifiable metrics, using “small business” may be required for economic structuring, but it limits how many leaders think about their own potential.

The opportunity to shift this narrative exists within events where the assemblage is comprised of small business owners. In these settings, use small business terms to target the promotional messaging, then find ways to release those technical terms at the event. Emcees, speakers, panelists, and staff can embolden the audience by using “small business owners” when necessary but then intentionally using more alternative titles that add depth to the attendee’s mindset. Instead of everything being focused on small, use synonyms that describe greatness, importance, appreciation, and yes, small business owners:

  • Entrepreneur
  • Founder
  • Leader
  • Student
  • Innovator
  • Heretic
  • Dreamer
  • Creator

    By using these synonyms, we can quietly inspire more inclusivity through fresh assimilation at events. Even if public policies remain rigid, more people will learn to celebrate and identify with more codifications.

    Over time, more people who may have kept themselves in a box will start to feel enlisted in all that is an entrepreneurial lifestyle. As more small business owners hear, use, and relate to enlivened vocabulary, the expanding taxonomy exposes new ideas, untapped resources, and unexpected realms to confidently explore within the local communities we love.

    Brewed From Within
    #36 📖 Leadership

    By Ben McDougal, ago

    Listen

    Listening is louder than it sounds.

    The more obsessed, the more vociferous we get. Idea machines must be willing to share compelling stories, but listening is part of any transmission. This is obvious, but with precious airtime up for grabs and knowing so much about our own interests, listening can devolve into feeling like a required distraction.

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    Hearing is passive.
    Listening is active.

    As we guide people through the layers of understanding, active listening forms a bond much faster than forcing ourselves to be heard. The fear of not having time to deliver our message will linger, but when we truly tune into what another person is saying, it shows we care. Active listening also helps us better harmonize our thoughts within the moment and counters the common mistake of overloading others with too much numbing details all at once. Knowing each conversation is part of a broader relationship journey, good listeners are almost always given a chance to make a bigger impact.

    Ready for an experiment? The next time you meet someone new, embrace your inner scientist. Set your introverted/extroverted mindset aside and focus your attention on asking as many thoughtful questions as you can. The less you talk, the better. This will feel awkward if you just fire question after question, so be concise with each response, then return to thoughtful questions for a more natural interaction. Consider expanding this social experiment by purposely doing this throughout an entire networking event. Remember who you talked with and track how the listening-focused conversations evolve. Over time, how do these relationships compare with others where you’ve been less intent on listening?

    Here are tactics to support your listening practice:

    • Center your internal attention.
    • Stay engaged with eye contact.
    • Use jarring questions to dodge small talk.
    • Don’t interrupt or jump to conclusions.
    • Occasionally paraphrase what was said.
    • Avoid the urge to make it about you.
    • Ask curious questions to go deeper.
    • Use non-verbal cues to express attention.
    • Record and share a few key takeaways.
    • Exit gracefully, without a sense of rush.
    • Follow up with one more question.
    • Ask about progress next time you meet.

    This type of active listening will not only extend your ability to hear. It will also make your responses more in-tune with what others are thinking versus always trying to prove your point. Selflessness may keep a conversation from landing exactly where we want in that moment, but as we move from one topic to the next, we learn how others work.

    Extra Shot

    Listening within a support network ignites optimism, connection, and motivation. A healthy balance involves listening to challenge networks, which keeps us intellectually humble and rooted in reality.

    When done well, an unspoken bond is formed. This synchronization curates future conversations that are enforced by shared enthusiasm.

    Brewed From Within
    #34 📖 Leadership

    By Ben McDougal, ago

    Playforce Principles

    People within a startup community and organizations throughout an entrepreneurial ecosystem often discuss the “future of work” together. As leaders transition today’s workforce into tomorrow’s playforce, the CIRKA equation helps us talk less and do more.

    Curiosity is what drives us to appreciate what goes into the answers. It keeps us asking how and why. Curiosity has always driven ingenuity, but as knowledge and solutions become so easy to find, it will be the curious who avoid mediocrity by exploring the edges.

    Initiative is a signal that shows you care. It’s showing up, raising our hand, keeping a promise, and sticking with it. The earlier initiative is shown, the faster trust builds. This allows initiative to stack, which increases impact over time.

    Real Skills help us all connect, communicate, and collaborate. First curated by Seth Godin, this evolving encyclopedia is an expansive list of modern credentials that go beyond our natural talents. Real skills shine through self control, productivity, wisdom, perception, and influence.

    Knowledge is foundational, specific proficiency required to do the work. For example, DJs need to know what knobs to turn, while doctors must understand human anatomy. Vocational knowledge may require formal education, but autodidacticism (being self-taught) is also an assessable path to transform anyone’s personal interests into know-how.

    Adaptability is knowing how to learn. It keeps us nimble, even when systems try to force rigidity. When change is constant, adaptability is what helps leaders remain versatile and relevant while also avoiding the pull toward mediocre.

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    Life is too short not to enjoy our time.

    Unquantifiable depth in each of these variables power the simplicity of the CIRKA equation. Energy guided by these playforce principles move us beyond loops that limit progress and ignite action on the timeline of now.

    By Ben McDougal, ago

    Hiatus

    Taking a break can nourish an artist and the seasonality of the art they’re creating. A hiatus can refocus teams or provide space for a community to recharge as well, but misplaced interruptions can also become an excuse to stifle progress.

    Let’s look at short breaks. For example, a moment to refill your mug, eat lunch, catch the latest episode of YDNTP, or get some sleep. When you’ve achieved flow, time away can feel like a waste of time. If a hiatus is only an excuse to avoid the work, then yes, worthless wandering is a trap and can actually devolve into a dangerous habit. When paralyzing progress is normalized, it will impact other things you actually want to accomplish. This means that even short breaks should be used to recharge your return.

    What about a more extended hiatus? This could be time away, setting a project aside, or even taking breaks in a relationship. When things get tough or positive momentum starts to fade, it’s tempting to avoid reality by pushing pause. This may keep things afloat, but it’s often a lackadaisical move to avoid reality, which may include the challenges of calling it quits. If an extended hiatus is truly strategic, the time should feel restful and build confidence as rearranged resources add fresh motivation. If this time away is wasted however, a false restart can be hard to recover from and will further expose what always needed to change. If a hiatus ever feels like an excuse to dodge blame, instead of being fainthearted, perhaps the illusion of an endless break should be replaced by a determined effort to make the bigger decision.

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    With limitless ways to spend our time, it’s easy to take on more than we should. Be careful taking breaks when you’ve overextended your own personal bandwidth.

    The length of any hiatus is relevant and so are the people who decide to take the break. Lone wolves can make these decisions easier, but they may struggle to understand the whole equation without feedback from customers, mentors, and fellow community members. When more people are involved, deciding what/when/how to take a break becomes more complex. For example, if a few people decide a break is good for a larger group, this decision may come from an individual’s lack of interest or bandwidth instead of what’s best for the group.

    When we feel significant, promises are kept and more people are set free to lead together. When we lead together, the limitations of some are less likely to compromise the well-being of many. This agency supports enrollment, trust, creativity, and honesty between more linchpins who collectively decide when the right type of intermissions will be most invigorating.

    By Ben McDougal, ago

    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, cultural) can each be hard to find, but celebrating what we have attracts more of what we want. As different types of capital connect, staying balanced with your personal bandwidth requires attention. But when we care and remain realistic, we give ourselves the permission to keep building.

    Uncharted crusades can also be dangerous. This quest will not go as anticipated and the opportunity cost is high, with endless ways to spend our time. Even when 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 and don’t be afraid to ask for help. There’s much to learn from heroes, mentors, and those you seek to serve. Success and failure leave clues, so speed up progress and avoid pitfalls by leaning into tribes you trust.

    When you’ve built without a map, the highs and lows strengthen decision-making. Practice also makes the unknown less intimidating. Experienced wayfinders gather feedback faster, measure the right metrics, and appreciate the hardships without allowing pride from the past to mislead them.

    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