Entrepreneurship

Professor X

Andre Wright is a genuine father, designer, visionary, activist, and community builder. He was inducted into the Junior Achievement Hall of Fame in 2021, with work featured at New York Fashion Week, and collaborations with Politico, NPR, Target, Atlantic Records, Warner Music Group, and Facebook.

Whether it’s Wright House, Humanize My Hoodie, or having dinner with Banksy, Andre has dedicated his life to the underrepresented. Listen as we jam on the hope for our youth, telling the story of a project to expand trust, and uniting a movement.

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By Ben McDougal, ago

Visualizing Variety

For people who play 80 hours instead of working 40, a diversified career portfolio often emerges.

A variety of activities and the contemporary energy of popcorning between them, helps vanguards stay ahead of the innovation curve. Diversification of work can also provide stability when the volume of different activities are strategically adjusted over time.

As we diversify career portfolios, balance, transparency, being realistic, patience, perpetual learning, and avoiding The Headline Trap is critical. These real skills fuel focused progress on multiple fronts and help reduce the risk of diluting yourself to mediocrity. If you’re stretched too thin, the value of diversification can devolve into fragmentation.

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It’s easy to discount our potential, but life is too short not to love what you do.

When change is constant, visualized assessment helps track how time is spent. Below is the evolution of my own career portfolio. People who see this often want to implement this method introduced in the Side Hustles chapter of YDNTB, so let’s jam on how to visualize your diversified career portfolio.

First, organize the things you spend time building. Assign a percentage of time spent on each activity, then plot the data into a pie chart. I use Apple Keynote to manage the pie chart and Adobe Photoshop for added flare, but any spreadsheet or slide deck software can visualize data in a similar way. Once created, save the pie chart as an image. You now have a conversation piece that showcases how you spend time. Update it as your career portfolio evolves or use this method as an annual exercise to stay balanced with your own personal bandwidth.

By Ben McDougal, ago

Triangulation

Cross-checking helps to determine distance, maneuver around obstacles, and identify rogue objects. Alongside the math, a triangulated team increases dependability.

Diversity of thought, talent, and real skills add synergy to accelerate progress and increase a team’s confidence when a problem is attacked from multiple angles. This nimbleness is leveraged as co-founders create a culture that makes each person feel significant.

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Building alone is easy.

Team up to make it fun.

On the prowl for co-founders? Consider triangulating a hipster (customer experience), hacker (technology), and hustler (business development). When these complimenting archetypes also blend hints of founder-market-fit, a timely curation gives any team exponential capacity.

To find missing links, connectors become connected. So show up and be quick to make interesting introductions. When the first degree of contact lacks obvious opportunity, remember it’s the second and third degree of connectivity that delivers precision. Over time, generosity in an entrepreneurial ecosystem expands and tightens 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.As teamwork begins, bonds that have formed naturally will support lasting collaboration with people you respect. That said, established trust is not an excuse to get complacent.

To nurture the power of triangulation be honest and transparent from start to finish. Every story ends, so don’t avoid difficult discussions. When structuring a business, agree on the terms, leave space for change over time, and maintain an operating agreement to ensure clarity with less tension. A commitment to abundant communication helps each team member remain attentive to details.

Professionals will take it further—inviting responsibility, then keeping the promise. For any idea maze, we take the blame, willingly give credit, and celebrate in style.

Lone wolves move fast but the expanded capacity of a team helps an odyssey go far. When a fun, long-term cast plays long-term games together, the chemical reaction can be an affinity toward work that feels like play. Cheers!

By Ben McDougal, ago

Echoes

The echo of an idea is always fading. How can we extend ideation long enough to activate early moves, blow through barriers, and maintain 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 kabillion factors. Still, let’s sip on the artistry of pushing without being pushy.

Start easy. Personally think through the various angles that might make an idea interesting. This private contemplation requires thought and time. Time is precious, and yet we waste it. The ease of your own thoughts will soon meet the hardships that await those who don’t let ideas breathe. This makes stealth mode precarious and early moves confusing, which makes ongoing customer discovery more important.

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Will you spend time or money?

When we share a new idea with someone else, the situation becomes complicated and complex. That is the moment we put our idea on a hook. It’s also when leaders push past fear and invite doubt. Connecting dots within such complexity is difficult, takes time, and is never straightforward. When the sacrifice is made, research builds confidence and adds clarity to how opportunities are articulated.

As thought through in the Isochronal riff, this makes the efficiency of blunt repetition tempting but ineffective. More of the same without execution—whether by co-founders, mentors, early adopters, or investors—only chases interest.

To avoid the fade, find diverse ways to motivate movement. For a fun visualization, imagine a glass pond. If one pebble drops in, the lonely ripple is loud and obvious but also fades fast. It makes a splash and is soon forgotten. Now, imagine many pebbles thrown in different ways, all around the pond, from every angle, and over time. The pond is now alive! The echo of each pebble is magnified, and the abundance of rippled collisions leaves a more lasting song.

Like a pond of pebbles singing together, leaders can nudge progress long enough to activate action. Conversation in different environments, inquisitive questioning, active listening, creative analogies, talking about anything else, releasing reluctance, and letting others lead are all ways you can keep building without getting too frantic. Intentional diversity allows each different echo of one idea to feel distinct and yet all bounce on a shared wavelength.

By Ben McDougal, ago