Entrepreneurship

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

                Storytelling

                Humans are innate storytellers. We use (sequenced) stories to enjoy life, relay ideas, and network experiences. Passed over generations, the willingness to tell stories has helped our species survive. When collided, shared understandings then summon diverse environments connected to thrive.

                As we narrow the narrative into an entrepreneurial lifestyle, the values of storytelling are felt as we learn, create interest, unite, and act beyond the shared moment. Over a brew, in the office, at events, out with friends, or on-stage, leaders must be able to translate the story of a business.

                The environment, industry, audience, and format affect how a story is told. The sentiment should be consistent, but your story won’t sound the same each time. Agility, preparation, and awareness will keep a story genuine, truthful, and engaging. Preparedness also boosts our confidence to share our stories in any situation.

                Internal storytelling between owners, co-workers, mentors, advisors, and customers is guided by listening, curiosity, data, transparency, and all that’s found in the Team chapter of You Don’t Need This Book.

                Let’s expand the repertoire with a focus on storytelling with strangers. This is done by playing with styles and tinkering with creative formats for the story.What’s your style? How casual can you make it? How nerdy can you go? What feelings do you evoke?

                Alongside different styles, timing also helps to format the story. One sentence is a sharp conversation starter. 42 Seconds is ideal for networking events and in small groups. 6 Minutes delivers details to support a valuable Q&A. 10+ minutes creates space for more depth, but don’t numb the audience. 45+ minutes is leading event sessions and keynote speaking.

                Along with talk, relatable assets bring a story to life. Such creation uncovers flow for a story. So embrace branding, social media, website development, slide decks, one-pagers, and endless types of physical and digital materials that connect storytelling with an audience that cares.

                No matter the situation, honest understanding, energizing enthusiasm, practice, transparent vulnerability, intellectual humility, and concise simplicity will serve you well. Nothing pushy, but pops of persuasion curate attention along the way. As a remarkable story comes together, feedback will sharpen the business and help tweak the transmission.

                By Ben McDougal, ago

                Momentum Mountain

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

                Extra Shot

                “Inspiration is perishable —  act on it immediately.” – Naval Ravikant

                Meaningful momentum is awakened in endless ways. Early momentum might 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. It only becomes more important. There are a world of examples, but growing the business, achieving milestones, and celebrating progress are all forms of valuable 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 entrepreneurial ecosystem.

                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 may be 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.

                Like the opening quote reminds us, inspiration is perishable. The longer stagnancy lingers, the further you get from momentum. Tactics to maintain kamiwaza, even when momentum is melting, start with communication.

                Honest communication adds clarity and is the easiest way to appreciate the realities of slowness. 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 may be able to 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 a real thought, but a tad boring. When it’s time to thrive, not just survive, sparks fly as initiative is taken.

                Tactics for climbing a momentum mountain include:

                • Connecting within startup communities
                • Traveling and learning something new
                • Saying “yes” to unlock adventure
                • Saying “no” to create space
                • Revisiting customer discovery
                • Building a new feature
                • Considering a pivot
                • Onboarding new customers
                • Adding to the team
                • Have fun, then staying centered on a climb down
                • Whatever else generates joy in your own life

                  Momentum is crucial to playing long-term games with long-term counterparts. Find a good pace by exploring the momentum you’ll need at different stages of the quest.

                  This awareness helps you quit chasing momentum and sets us free 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.

                  By Ben McDougal, ago

                  Aphorism

                  Personal truths on health, life, wealth, and happiness evolve from entrepreneurial endeavors.

                  The pursuit of building a business causes people to be more contemplative about other aspects of life. Learning to articulate thoughts as a leader is transformative. Knowing ones self can be parlayed with mindful aging to create curiosity that can be mixed into heartfelt conversations.

                  How we explore big ideas depends on the environment, people you interact with, and knowledge you pursue. This makes me thankful for my own entrepreneurial experiences, but more important, the immeasurable blessing it can be to expand our minds by plugging into startup communities and entrepreneurial ecosystems.

                  A willingness to show up and the trust built through such generosity has allows leaders to become apart of so many other startup stories. As mentioned throughout YDNTB, consistent action over the long run is required, but insight learned along the way provides a path to understanding for anyone, on almost any front.

                  As we support entrepreneurs through the art of connection, the invitation to have more diverse discussions is unlocked more often. Whether it’s strategic, tactical or philosophical, what a gift toward open-mindedness this becomes.

                  Along with stimulating conversations with agreeable peers in a support network, Adam Grant reminds us that it’s important to weave in the perspectives from a challenge network as well. Challenge networks consist of disagreeable people we trust to point out blind spots. This helps to overcome weaknesses with critical feedback we may not want, but need. Peculiar interactions within a challenge network also unlock humbling opportunities to be wrong. Intellectual humility helps avoid misguided confidence and brings us closer to different forms of truth.

                  Extra Shot

                  Smart people change their mind all the time. Find joy in discovering you were wrong and now less wrong than before. This is not incompetency. It’s being honest, respectful, and willing to learn.

                  By Ben McDougal, ago