Entrepreneurial Lifestyle

Brad Feld

This Season 2 Finale features an extended conversation (2+ hours) between Brad Feld and Ben McDougal, recorded in the wild, LIVE from the mountains of Boulder, Colorado!

We begin with a rewind on Brad’s own journey, then shift into entrepreneurship, leadership within startup communities, and venture capital in the first hour. Ben teleports to narrate a break with two writings inspired by Brad, then we dive back in for so much more. The origins of Techstars, technology, mentorship, and philosophy is how we land this milestone moment.

As you’ll hear/see, EP100 brews timeless insight for founders and the entrepreneurial lifestyle. Enjoy the full experience, and to make key takeaways easier to share, bookmarks for this extended experience are highlighted below. Cheers to another remarkable season of You Don’t Need This Podcast and let’s keep building… together.

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0:00 – Ben in Boulder
1:30 – Hello Brad Feld
2:30 – Early Experiences
5:15 – Writing First Book
7:00 – Incubator to Accelerator
12:40 – Random Days
29:30 – Startup Communities
36:15 – Entrepreneurial Ecosystems
37:30 – Too Many Referees, Not Enough Boxers
38:15 – Rural Startup Communities
43:30 – Astronomy
45:30 – Positive Sum Games
46:15 – Give First Intrapreneurs
50:45 – J-Curve
52:00 – Venture Capital Timelines
54:00 – Investor Metrics
56:30 – The Measurement Trap
1:01:15 – 5 Why’s
1:03:50 – Cliffhangers

1:04:50 – Break ☕ #GiveFirst
1:08:18 – Break ☕ Intrinsic

1:11:50 – Welcome Back
1:12:25 – Founders of Techstars
1:23:00 – Startup Community Partnerships
1:33:20 – Guitar Hero in Times Square
1:38:15 – Bigger Isn’t Better
1:41:00 – Sclerotic Thoughts
1:42:00 – Contentment
1:42:50 – BEN BOT
1:44:05 – Digitized Consciousness
1:45:12 – Vibe Coding
1:46:45 – Dinostroids
1:49:40 – Quantified Self
1:54:16 – Biohacking
1:56:30 – AI Notetaking
1:59:55 – Founder’s Interest in Philosophy
2:00:50 – The Entrepreneur’s Weekly Niche
2:07:10 – Obsession over Passion
2:10:20 – Affinity as an Investor
2:11:35 – Fight to the End
2:11:50 – The Dip -Seth Godin
2:12:20 – Successful Companies Experiment
2:13:15 – Evolution of Work
2:14:30 – Quickfire
– Spell Check
– Ant Hills
– Signal to Raise Capital
– Long Run Epiphany
– Being Alone
– Pinball Wizard
– Music & Concerts
2:23:15 – Fine Art
2:24:30 – You Don’t Need This Book
2:26:00 – “They can’t kill you, and they can’t eat you.” –Len Fassler

Give First.
People like us.
Do things like this.

BONUS MATERIALS

https://feld.com

https://foundry.vc

https://techstars.com

Break: #GiveFirst + Intrinsic

http://BradFeld.YouDontNeedThisPodcast.com

EP14 – Drams of History 🎙️ Tej Dhawan

EP18 – Fourteeners 🎙️🎞️ Jeff Reed

EP29 – Borderless 🎙️ Kerty Levy

EP56 – Caffeinated Manifesto 2 🎙️🎞️

EP99 – Traveled 🎙️🎞️ Trevor Carlson

https://BenMcDougal.com/tag/Brad-Feld

https://BenMcDougal.com/tag/Techstars

http://YouDontNeedThisPodcast.com

By Ben McDougal, ago

Traveled

Trevor Carlson visited 50+ countries in 5 years!

He’s also a friend, founder, content creator, and below-average salsa dancer. Pack your bag and ride along as we wind through an extended episode with wild stories from around the globe, a narrated break, writing fiction, thoughts on the future of You Don’t Need This Podcast, experiential wisdom brewed to keep us building together, and bonus footage where Ben shares what he wants from life.

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LISTEN on SPOTIFY

BONUS MATERIALS

https://lostandlore.com

https://FreshFuelMarketing.com

The Climb by Trevor Carlson (early access)

Roasted Reflections Break: Serendipitist

http://Traveled.YouDontNeedThisPodcast.com

EP44 – Do What You Love 🎙️ Scotty Russell

EP56 – Caffeinated Manifesto 2 🎙️ Ben McDougal

EP84 – Base Camp 🎙️ John Kallen

EP94 – Paving Paths 🎙️ Eric Engelmann

Man’s Search For Meaning -Viktor E. Frankl

http://YouDontNeedThisPodcast.com

YDNTP on YouTube

http://BENBOT.ai

By Ben McDougal, ago

Gig Economy

Derreck Stratton is a military veteran and startup founder who connects doers to odd jobs. Instead of asking “who do you know” for a task around the house, the HUDU team built an easier way to find handy folks looking for side hustles nearby.

Like ride sharing, this episode highlights more examples of how the gig economy is evolving. We chat about trust within a two-sided marketplaces, building as a non-technical founder, content creation, and paving a path to go far with activities that look like work to others, but feels like play to you.

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LISTEN on SPOTIFY

BONUS MATERIALS

https://heyhudu.com

https://info.heyhudu.com/gig-economy-2-0

http://Gig-Economy.YouDontNeedThisPodcast.com

Roasted Reflections Break: Uncertainty

EP34 – Measured Twice 🎙️ Ryan Glick

EP44 – Do What You Love 🎙️ Scotty Russell

http://YouDontNeedThisPodcast.com

https://tesla.com/we-robot

http://BENBOT.ai

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 take action 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 effects how a story is told. The sentiment can remain 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, understanding, 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 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 helps to format the story. One sentence is a sharp conversation starter. 42 seconds is ideal in a small group. 6 minutes delivers enough 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 the flow for a story, so embrace branding, social media, website development, slide decks, one pagers, and endless types of physical and digital materials that connects 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 continue to tweak transmissions.

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