Entrepreneurship

Shifting Gears

Imagine the howl of a distant motorcycle bolting through the night. Hear the speed and wait for that clutch to drop, knowing more power awaits.

The first gear is dedicated to initiating motion within an engine. It won’t get you far, but as the red line wraps, a shift brings you into the next gear that builds on the momentum. As that next gear tops out, yet another shifts moves you farther, with higher gears that bring you to full speed.

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After pushing a motorcycle to 150mph, twas time to sell that bullet on wheels. A face full of wind is still invigorating, but a convertible will now suffice.

Any journey is a dance, but reaching your destination requires an ability to temporarily lose power in exchange for more lasting capacity. Whether it’s personal or in business, recognizing a limit prompts a well-timed shift in gears to keep moving forward.

Brewed From Within
📖 Entrepreneurship

By Ben McDougal, ago

Momentum Mountain

From the moment we decide, a force is required—action geared to find and then maintain momentum.

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Everyone has a creative spirit. When an appetite for (calculated) risk is applied, the entrepreneurial spirit emboldens.

Meaningful momentum is awakened in endless ways. Early propulsion can mean showing up at an event for the first time, researching the competitive landscape, testing an early hypothesis, leaning into customer discovery, considering potential co-founders, building product, and eventually activating a launch sequence.

Once a project is launched, the need for momentum gets stronger. There are a world of examples, but growing the business, achieving milestones, and celebrating progress are all forms of momentum.

Even in later stages of a company, momentum drives activities like succession planning, navigating exit paths, and considering how your human, financial, cultural, intellectual, and network capital can be recycled back into the startup community.

If momentum is maintained long enough, the result can be a flywheel effect that feeds on itself. Most things you want to grow require attention, but with less friction, momentum delivers bonus time and valuable understanding. Space for new activity emerges and that keeps things interesting.

The tough reality is that if momentum is melting, it’s difficult to recapture. Once something melts, it’s never quite the same. These dips are moments to consider when and what to quit. If there’s enough energy to keep going, there may be a way to keep building.

The longer stagnancy lingers, the further you get from momentum. Tactics to maintain kamiwaza, even when momentum is melting, start with communication.

Honest communication spells out the pace. Reducing the weird by exposing the why also keeps different stakeholders on the same page. By reducing the tension that quietly brews in silence, teams can run at lower speeds, even during lethargic times. If left unattended, however, this can devolve into a lack of urgency that brings another set of challenges.

At lower speeds, perhaps less movement is needed to regain the sense of shared momentum? That’s true, but also lame. When it’s time to thrive, here are climbing tactics to awaken the mountains of momentum:

  • Say yes to unlock adventure.
  • Say no to create space.
  • Travel to expand the mind.
  • Share premium human time.
  • Revisit customer discovery.
  • Experiment with new ideas.
  • Onboard new customers.
  • Build a fresh feature.
  • Add to the team.
  • Consider a pivot.
  • Alter your routine.
  • Embrace continual learning.
  • Expand your engaged network.
  • Attend a new startup community event.
  • Revisit an activity you once enjoyed.
  • Stay centered on any descent.

    Momentum is crucial to playing long-term games with long-term counterparts. Find the proper pace by recognizing the momentum you’ll need to move through different stages of the quest. This awareness helps us quit chasing momentum and frees us to forge better art at a sustainable speed. Continue to multiply mass and velocity, which equates to momentum when, where, and how it’s needed to stay wild.

    Brewed From Within
    📖 Entrepreneurship

    By Ben McDougal, ago

    Feedback is Data

    Customer discovery paves the path to profitability.

    This really is the work for entrepreneurs starting a new business. Customer discovery requires trust in your early moves, obsessive curiosity, patience, thick skin, humility, an interest in being wrong, discernment, and a willingness to adapt. No problem, right?

    For many entrepreneurs, impartial feedback can be scary. Customer discovery puts ideas on the hook, and colliding new conversations may contradict past assumptions. That’s the point! Interacting with the market you seek to serve allows us to learn from no in a way that gets us to yes.

    As you collaborate with those who criticize what you’re building, learn why naysayers debate your hypotheses. Be humble. Either attack the massive lift to change the product and even the target customer or make your concept more compelling to win over those who care.

    The more you learn from others, the more you’ll recognize supply and be able to meet true demand. Collecting real-world data is human and intellectual capital that attracts more network and financial capital. 

    Beyond the psychology of it all, customer discovery can feel like a drag because it is often a protracted process. The time commitment is real. This market exploration can be slow at first and may seem less necessary as signals of traction emerge. The potential need to rethink ideas makes feedback scary too. As always, if the entrepreneurial lifestyle was easy, career nirvana would not be so fleeting. Knowing this, we can seek honest feedback that strengthens our value proposition to eventually go further in the right direction.

    When learning from the perspective of others, it’s imperative to remember that feedback is data.

    Collect, organize, and examine data from feedback like a scientist. Inference is more informed with data. Decisions that are made become more in tune with reality as you continue to collect and learn with data.

    As you translate decisions into action, you must also find your own way. Even with good intent, people who provide you with feedback are doing so based on their experience. The experience of others is based on their own past, and no feedback is likely to fully harmonize with your vision. There are many ways to navigate the idea maze. Gather feedback like power-ups in a video game and use diversified data to guide your quest toward product-market fit.

    By Ben McDougal, ago

    Prismatic

    There are endless early moves to help avoid pushing your idea toward someday. For instance, creative wireframing requires only a pencil. With a little visualized clarity in place, a couple exploratory conversations can also help.

    First, meet with a mentor. This should feel like a supportive space but avoid rainbows and butterflies. Be realistic with exciting aspects of the idea, but also the challenges. As we learned in YDNTB, an early no is much better than a long, wrong yes. That said, playing it safe is easier than activating initiative, so don’t let early doubt slow you down. Instead, welcome it. Let curiosity uncover new understandings. Pivots are inevitable, and this exploration adds confidence as the original idea is tweaked toward product-market fit.

    After transparently talking with that trusted mentor, the next meeting is with a potential customer. This will feel too early, but it’s not. You’re actually protecting your personal bandwidth by not swinging at a bad pitch too many times.

    To optimize early innings, arrive prepared to ask good questions. Take notes and speak less so you can actively listen to how this potential early adopter is responding.

    Are you building a pain killer or vitamin? Remember, feedback is data, and this is only one data point, but let this conversation infuse reality into the idea. Show up, stand out, follow up, stay connected, find a thoughtful way to accelerate their work, and then keep building.

    The business model canvas is a tool to do so. While it’s impossible to predict the future, business model canvases help us continue to explore while curating a story that sells.

    Most early business ideas don’t have a clear story. This can make it hard to know where to start within the business model canvas. While you can use this tool in endless ways, consider an approach that is less about the entire business and more about one story at a time. Instead of trying to boil the ocean, organizing a complete story for each customer segment creates a combination of more actionable insights.

    To give it a try, use this special business model canvas. The areas are numbered to curate canvases that each highlight a customer story:

    1. Customer Segments – Start with the details of a particular type of customer. The goal isn’t to complete the Customer Segments box. It’s starting a story to follow through the rest of the canvas. Now lean into the pain as you move from box to box and watch as your solution transforms into a story.
    2. Value Propositions – What benefit(s) can you deliver?
    3. Channels – Where can you connect with this customer?
    4. Customer Relationships – Who are you working with and how will you make this customer feel?
    5. Revenue Streams – Will financial income flow? How?
    6. Key Activities – What actions make the customer care?
    7. Key Resources – What is needed to keep building, and how might needs change to maintain momentum?
    8. Key Partners – Who helps to make this sustainable?
    9. Cost Structure – What costs go into activating this customer segment? How is pricing organized to support realistic profit margins that align with a financial model?

                  By telling the story of created value for one customer segment, hypotheses can be connected with context. Next, using a separate business model canvas, visualize more stories based on different customer segments.

                  With separate business model canvases for each customer segment, merge everything into one business model canvas. To stay organized, select different colors to use for each customer segment. As everything blends together, the prismatic rainbow maps roads to reality.

                  By Ben McDougal, ago

                  Down Under

                  It’s easy to think the perfect investor pitch exists.

                  The inspired business idea, sharp slide deck design, magical lines within a concise pitch, and formulas to make everything click. Study fundraising all you want, but the art form can be seen when understanding adds space for storytelling that shows instincts.

                  EXTRA SHOT

                  This contribution was written by Saba Karim. This Australian technologist is a perpetual builder who has heard more business pitches than anyone you know.

                  During my time at Techstars, we listened to hundreds of founder pitches. Different industries, backgrounds, and levels of experience. On paper, many of the companies looked nearly identical. Similar markets, similar traction, similar slides. Yet the outcomes were rarely the same. Some conversations created momentum immediately. Others stalled, even when the numbers looked better.

                  The difference was almost never the product. It lived in the story. The strongest founders were not reciting information. They were explaining how they saw the world. Their judgment was heard in the way they framed problems and talked through decisions. Their pitch was not something memorized. It was something the founder(s) understood. That distinction matters, because investors are not betting on slides. They are betting on decision makers. A deck can show intelligence. A story reveals instinct.

                  Many founders treat pitching like a checklist. Hit these slides. Answer these questions. Say the right words. But when either side approaches an early interaction that way, the conversation usually falls flat. No deck is ever complete enough to replace connection.

                  When founders realize alignment matters more than perfection, the dynamic changes. The meeting stops feeling like a performance and starts feeling like a conversation. That shift alone creates momentum.

                  Momentum is not mysterious. It is human. Founders who walk into meetings with clarity tend to leave with more doors open. Not because everything is perfect, but because belief compounds quickly. You can feel when someone has their right foot forward. 

                  They are not rushing.
                  They are not over-explaining.
                  They speak in present tense.
                  This is what exists today.
                  This is what we’ve learned.
                  This is what we are doing next.

                  Reality builds more trust than ambition ever will.

                  Another common mistake is trying to sell the product instead of the opportunity. Features matter, but they rarely carry the conversation. What resonates is why the problem matters, why the timing makes sense, and why this founder cannot walk away from it.

                  The best meetings barely felt like pitches at all. They are calm, low pressure conversations. Sometimes there was a deck. Sometimes there was just a demo. The tone shifted from here is what I want to build to here is what I have already built. That shift changes everything.

                  As founders, we tend to overthink the wrong details. Being slightly late. A noisy background. A moment of nerves. Those things rarely matter. What does matter is presence. Listening instead of talking. Answering the question that was asked. Slowing down enough to think clearly.

                  Extra Shot

                  Confidence is not volume. It is calm.

                  Over time, storytelling stops being a fundraising skill and becomes a life skill. Entrepreneurship demands it constantly. With investors, teammates, customers, and yourself. Every difficult decision needs a narrative strong enough to carry uncertainty.

                  Early on, those stories are mostly aspiration. Later, experience reshapes them. Obsession sharpens them. Failure humbles them. You stop trying to sound impressive and start trying to sound honest.

                  Eventually, you care less about winning every room and more about finding rooms where you belong. Fundraising becomes relational. You are no longer trying to convince someone to believe in you. You are discovering whether you already believe the same things.

                  People do not want to feel processed, optimized, or pitched. Success, whether in business or in life, is rarely about winning someone over. It is about how people feel when they leave your presence. The energy you bring into a room. The care you show when no outcome is attached.

                  In the end, the perfect pitch never existed. What existed was clarity, presence, and the courage to speak from experience instead of expectation. There is no finish line. Only better questions, deeper alignment, and the quiet understanding that the best relationships are all built the same. With intention, kindness, and a genuine desire to be remembered for how you made people feel.

                  By Ben McDougal, ago