Roasted Reflections

2 Hours

Greg Horowitt is a social architect and pracademic. He is an accomplished entrepreneur, investor and global advisor. I always knew of Greg because he co-authored The Rainforest with Victor Hwang. After years of learning from Victor, I decided it was time to connect with the other half of this intellectual equation. I reached out to Greg and he was generous enough to setup a time to chat. We had no agenda, but ended up talking together for two hours!

This extended discussion allowed me to enjoy fun anecdotes about a bestseller so many entrepreneurial ecosystem builders have on their bookshelf. I learned about Greg’s innovation design role at UC San Diego and his upcoming book about the religion of innovation too. We riffed on entrepreneurship, venture capital, innovation ecosystems, complex adaptive systems, how humans think, economic development, the speed of trust and how storytelling brings everything together. Here is a Twitter thread with our photo and a few more memorable moments, but having Greg Horowitt lob knowledge grenades my way was such a treat.

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Meaningful discussions can form faster without an agenda.

This enlightening interaction has me reflecting on how a hint of initiative unlocked another cool connection. Also, how that extra hour gave Greg and I time to discuss a variety of topics with space for this thoughtful exploration to go deeper. Look at your bookshelf or social media feed. All of us have giants we’d love to meet. Do you seek out learning sessions with people you admire? How might a significant conversation evolve if you give it an extra hour to develop?

We’re all busy, sure, but a peculiar conversation is rarely a waste of time. Perhaps it’s only done occasionally, but more cerebral conversations allow us to go beyond protecting our knowledge with fancy jargon. Perpetual learning with a coexisting effort to accelerate others will release innovative energy that sparks creativity and reveals a path to deconstructed understanding.

By Ben McDougal, ago

Love Triangles

As we celebrate our love for one another, Valentine’s Day felt like a heartfelt time to reflect on building a business with and around members of your family.

The permanence of family leads to many business partnerships. Some operations pass from one generation to the next. Others spawn when family members decide to start something new. Still more businesses come together as people create new family bonds and merge their work into love triangles.

It seems obvious to start something with those you love. In some cases, the convenience makes it easy. In other cases, it can become a necessity to turn the family into a team. No matter the why, transparency and trust within a family is hard to beat. This allows family members to wholeheartedly lean on one another. Such an unwavering ability to count on each other is why family businesses always have a chance.

While family businesses can thrive for generations, there are dangerous downsides as well. Not everyone who loves each other should work together. Home and work are often like night and day. The difference between the two makes each one better. Living and working with family makes it hard to separate the two. This can lead to arguments that extend far beyond the office. These inescapable emotions can damage relationships and bleed into the broader team. While you’ll spend the most time with your family, building a life together doesn’t mean you have to work on the same thing. A healthy amount of individuality allows each person to do more and space makes coming back home even sweeter.

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Do you work with family? If so, share your best tips in the comments! Also, did you know Brad Feld and Amy Batchelor wrote an entire book on this, called Startup Life?

Whether you build a business together or not, family dynamics affect all entrepreneurs. The most direct impact comes from your significant other. Your co-founder in life has a huge influence on your ability to thrive as an entrepreneur. Almost like separations of power, each person can provide contrasting perspectives, honest feedback and valuable support to balance the time, financial and emotional responsibilities of life.

Co-founders in life who share authentic trust give each other stability, fewer restrictions and more opportunities. If you find the love of your life, help them be their best. Admit they are the better half and be humble enough to let them return the favor. Such motivation from inside the home fuels a deep sense of abundance. The result is a more determined mind, body and soul eager to learn from the person who knows you best. This constant support brews loving vibes that spill into your work. Two people who push each other to be better than they would have been alone is the ultimate gift.

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To love is to share life together,
to build special plans just for two,
to work side by side,
and then smile with pride,
as one by one, dreams all come true.
The Meaning of Love – Krina Shah
By Ben McDougal, ago

Super Sentence

Modern gladiators went to battle last weekend and it only took around 11 minutes for the Tampa Bay Buccaneers to win Super Bowl LV. It’s interesting to compare such a small window of actual gameplay to the endless pregame analysis, commentary, predictions, production and post-game highlights.

With two weeks leading up to game day and another week highlighting this annual event, the Super Bowl experience basically lasts three weeks. That’s up to 30,240 minutes of potential attention the NFL can earn from each consumer. With those 11 minutes of live action only representing 0.04% of this three week long spectacle, clearly the Super Bowl is about more than professional football. It’s about the host city coming to life, a stadium full of fans, the TV commercials, the halftime show, the food and everyone sharing the Super Bowl together.

This is not by accident. The NFL understands their audience. They’ve achieved product-market fit and since 1920, have built around what they do best. This entertainment behemoth does American football really well, but $15 Billion in annual revenue doesn’t come from 150 snaps per game. It comes from being the best at one thing, then expanding on that with complementing (and profitable) activities. This has strengthened their existing fan base, created opportunities to increase their audience and transformed their product into a cultural phenomenon.

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If your company was given a free Super Bowl commercial, who would be your target audience? What story would you tell? What action would you want viewers to take and would you be ready to convert attention into trust when they took that action?

The NFL makes product-market fit look easy, but building something that satisfies true demand is harder than it sounds. Avoid getting sacked by admitting your idea isn’t special and that the future of your business relies on your ability to consistently execute. Trust that early success relies on clarifying your value proposition, evolving your business based on continued customer discovery and your ability to collaborate with those around you. This takes finesse, thick skin and a special combination of urgency mixed with patience, but as you secure more paying customers, you may be given a chance to broaden the impact.

Can you describe what you and/or your company does best in one sentence? Hit me with it! If you send me your own super sentence, I’ll connect you with someone who can get you to the next first down.

By Ben McDougal, ago

Pure Wonder

Children embody a state of wonder that entrepreneurs can learn from.

They wake up each morning without a plan. They have no preconceptions. No judgments. No worries. A lack of expectations allow kids to naturally live in the moment. They get excited about the little things and cry over nothing. Their states of pure wonder is fascinating.

Now, fast forward 20 years. The world hardens us. We want to impress and make our mark, but life can feel exhausting and the need to make ends meet adds constant stress. Our experiences make us more intelligent, capable and aware of our surroundings, but they also limit our ability to feel pure wonder.

As you’re building a business, release from the daily grind by thinking like a child. Pretend you were born yesterday. Be silly once in awhile. Forget the agenda. Color outside the lines. Get weird to solve problems. Laugh at your mistakes. Play in your sandbox and have fun getting messy. Let a child-like sense of wonder shrink your ego to make room for what’s next. What you’re building matters and if your work allows you to feel pure wonder, be thankful and pass it on.

By Ben McDougal, ago

Personal Bandwidth

New projects make work invigorating and it’s fun building things we care about. When we’re all able to do so much more with less in our connected era, the danger becomes how easy it is to spread yourself too thin. If you seek to unlock the boundless energy from a balanced career portfolio, it’s critical to keep an eye on your personal bandwidth.

To make it easy, visualize all the work you do as a dynamic pie chart. Each project you’re involved with represents one slice. It’s not an exact science, but the more time, money and energy you spend on something, the larger that slice becomes. Let’s call this your career portfolio.

Most of us can manage multiple slices of activity within our career portfolio. For example, a traditional, salaried position may be the lion share, but there’s still room for that innovative idea at your company, a little side hustle, the volunteer role and mentoring a few other entrepreneurs. No matter what makes up the complete pie chart, stay mindful of the coevolving sizes of each slice and how everything interacts within the overall system.

Saying yes or no to new projects should obviously be carefully considered. As you make these decisions, be honest with the resources required to continue building on each front. The time you spend on one thing can’t be spent on others, but positive force in one area often fuels fresh energy (and clarity if it’s time to quit) for other areas of your career portfolio. When different projects are in the same realm, synergies may be easier to compound, but sometimes having projects in completely different industries provides stabilizing diversification.

Beyond the obvious impact of adding or removing elements within your career portfolio, how resources are spent on existing areas of your career portfolio should feel strategic. Think about how much time is being spent compared to the income that’s being produced. There are other factors to consider too, as we know it’s not all about the money. Reflect on the type of energy each project generates. Who do you get to work with and how does the work make you feel overall? Hobbies that pay just enough to break even, leading a group of people you care about or volunteering to become a mentor are all wonderful examples of satisfying additions that don’t pay the bills.

Have something that’s dragging you in the wrong direction? It’s hard to revive old projects, but don’t be afraid to put things on the back burner. That said, if it is time to quit, read The Dip by Seth Godin, then decide if and when to make your move. Winners quit all the time, they just quit the right things at the right time.

That last sentence reveals one more important variable: good timing. When you activate new projects, adjust resources or quit something to make space for what’s next, good timing will provide a noticeable blend of confidence and tranquility. This state of mind will allow your work to make a bigger impact. To give yourself room to find good timing, remember entrepreneurship is not a race. Urgency is helpful because it creates valuable momentum, but stay patient knowing that persistence is the ultimate wild card.

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I once had a boss tell me I could never catch two rabbits. That’s outdated. With a balanced career portfolio and the support of those around you, we’re all able to catch more proverbial rabbits without diluting ourselves to mediocrity. Learn to efficiently activate different energies, on different projects, with different people, at different times, that all connect through you.

By Ben McDougal, ago