Entrepreneurial Lifestyle

Anxiety

The mind is divine. It gives us superpowers, and the dots we electrochemically connect make us human. Such capacity allows us to achieve extraordinary things. At the same time, this mysterious grey matter can also hold us back and even cause havoc.

Anxiety is assuming failure in advance. As a mental cousin to fear, anticipation, worrying, and perhaps even desire, anxiety is like an unspoken agreement you make with yourself to be unhappy until you get what you want.This exhausting emotion is all in your head, yet the way anxiety affects your body is absolutely real.

For those who pursue greatness, the more we try to achieve, the tighter we wind the strings of life. When harnessed, this fuels strength, creativity, grit, and persistence. As the tension tightens, however, something is bound to break. Healthy habits and being mindful of your personal bandwidth reduces the frequency and severity of such breakdowns, but with the relentless pressure from never-ending progress, it seems impossible to completely avoid disquiet.

The most common way we attempt to manage such angst is to stop the pain by seeking reassurance. The nourishment of overthinking every scenario in an unknown future may satisfy the moment, but scratching this itch usually makes things worse. Even if we answer every possible question, the willingness to indulge the worry sets a precedent that keeps you coming back to what can become an endless loop.

An alternate approach is to acknowledge the suffering. Don’t run from it. Appreciate the relentless internal narrative you’re dealing with. Breathe. Be thankful for having something you care this much about. Find peace in knowing you’ve done your best to tip odds in your favor, but invite doubt and welcome an opportunity to be wrong. The anxiety is here and it’s dramatic, but it’s also normal. Let thoughts float by, focus your attention on what’s good, and allow time to heal the pain. Yes, this is like letting a forest fire burn without soothing it with water. It will get wild at first, but it eventually burns itself out. The scorched land is then ripe for renewal and less likely to burn again.

Extra Shot

Accepting that anxiety is inevitable

may be a secret to finding equanimity.

By acknowledging anxiety, clarifying awareness helps us understand, even appreciate, the energy. This breaks the cycle and reduces the frequency of such misery. Courage over fear also adds an eagerness to lean on support systems, confirms confidence in how the pain will pass, and allows the mind to stay centered with less climactic swings.

Brewed From Within
#96 📖 Life & Happiness

By Ben McDougal, ago

Head Start

The entrepreneurial lifestyle resists definition.

Business owners paint with strokes of curiosity, determination, and innovation. When people build with creative ambition, experience is valuable, but the symphony of desire and attitude plays an equally important role. It takes heart to start and resilience to execute early moves, manage focus, build teams, maintain sales, and provide lasting customer service to maintain momentum.

The best part about an entrepreneurial lifestyle is that it’s accessible to everyone. This can be seen as students explore projects that transcend the classroom. It’s intrapreneurs fueling positive change in existing companies. It’s startup founders achieving product-market fit with new ideas and others who acquire an established business.

EXTRA SHOT

This contribution was written by Sheldon Ohringer. Along with helping us buy a business, Sheldon is an investor and board member who led large sales teams, developed acquisition programs, and as CEO took a technology company public.

Starting a brand new business is one way to explore the entrepreneurial lifestyle, but buying an existing business is also an interesting way to write your own story.

While there may be a higher cost for the head start, acquiring an existing business presents an interesting side door to the entrepreneurial lifestyle.

Organic growth is important, but there are added benefits in augmenting internal development with external acquisitions as well. As you consider a business to buy, avoid future headaches by understanding industry requirements, such as licenses, permits, zoning, and environmental requirements. As you work with existing ownership to determine a purchase price, a valuation based on capitalized earnings, excess earnings, cash flow, and tangible assets are all methods to guide fair negotiations. In the end, the right price is one that delights the seller and excites the buyer.

As details come together, partner with legal and accounting experts who focus on mergers and acquisitions (M&A) to document the transaction. A letter of intent, confidentiality agreement, contracts, leasing documents, financial statements, tax returns, and sales agreements are all important documents to talk with your M&A team about. Many transactions include a vesting schedule as well, so stay in tune with these details to avoid unwanted surprises.

There are a variety of strategic ways to acquire a business, but once the transition takes place, new owners are given keys to a kingdom that hails an established team, customer base, and operating procedures. As we see in the Exit section of the Results chapter in YDNTB, there will be challenges during these transitory times, but in the end, virtuous leaders listen to keep the culture balanced.

All the good that comes with a business is important to maintain, but an audit of negative aspects is important too. This focus on areas that need improvement is stressful, and concerned employees may exaggerate issues to make their own contribution seem important. To stay proportionate, talk with everyone for context, invite resolutions that may solve issues, get hands-on, and stay optimistic to keep your assessment honest and weighted against the big picture.

Searching and finding undervalued, cash-flow businesses may take time, but it serves as a viable alternative to growing a business from scratch. Intentional candor with areas to improve allows new owners to build on past success while charting a renewed vision for lasting prosperity.

By Ben McDougal, ago

Waiting Rooms

The waiting room is that season where you’re not where you used to be, but you’re not yet where you want to go. It’s the in-between. The pause before your name gets called. The place where you’re preparing for what’s next, whether you think you know what’s next or not.

If we can move our egos out of the way long enough, we’d see the beauty here. The waiting room is where character develops. Where preparation happens. Where we create, reflect, and release what no longer serves us.

But we want to bypass it. We grow impatient and intolerant. We think our will—our force—can push us through faster. It doesn’t work like that. You’ll only exhaust and burn yourself out.It’s easy to watch others get called before you. The mental chatter starts: “When will it be my turn?” “Will I ever be ready?” “Why them and not me?”

The problem with watching others is that you have no idea where they are in their journeys. You don’t know where they’re being called to next—or what’s waiting for them when they get there. Their timeline is not a reflection of yours. It never was.

Everyone gets called at exactly the right time for their highest good. Not a moment sooner. Not because the universe is withholding opportunity, but because love doesn’t set us up to fail. The waiting room keeps us from walking through a doorway we’re not ready for. It’s protective. We wouldn’t hand a six-year-old the car keys just because they felt ready to drive. Your higher wisdom knows better. That child stays in the waiting room until they’re actually equipped for what’s next.

EXTRA SHOT

Watch Vanessa narrate this riff on-stage!

No one wants to be in the waiting room. But everyone has to pass through it. These built-in pause points aren’t punishments—they’re where we catch our breath, integrate what we’ve learned, and prepare for what’s coming.

We take the wait personally. Like it’s evidence we’re not good enough, not ready enough, not deserving enough. We get frustrated. Resentful. Sometimes we give up right here.

But your job is to learn to sit in the tension of not being where you want to be without making it mean something’s wrong with you. When we are able to loosen the grip, the pause can be strategic. You can recalibrate here. Gain mastery here. Rest here. The waiting room is the bulb that leads to the flower—fertilized by your patience and who you choose to become while you wait.

EXTRA SHOT

This contribution was written by Vanessa McNeal. Vanessa is a social architect and keynote speaker who transforms the nervous system to lead through love.

Life is full of waiting rooms. When the time comes, we move forward and eventually, we find ourselves in another waiting room. We create suffering if we believe we’ll arrive one day at a place with no more growth, no more waiting.

That’s not how it works. What would we learn by skipping the journey to reach the destination? How would we develop patience, self-trust, or resilience?

Right now is transitory, but micro-moments add up and coalesce into the story of our comprehensive progress. Waiting rooms are where we become the person who’s ready and open to what comes next.

By Ben McDougal, ago

Table of Riffs

Brewed From Within: Energy for the Entrepreneurial Lifestyle compiles 125 riffs into four timeless sections. Here’s a VIP snapshot tour, with a handful of riffs linked for early access!

Imagine holding your new book. After the cosmic cover art is initially observed, we open to a title page, one blank page for personalizations from the author, and then the publisher’s copyright page. After the heartfelt dedication page and motivating preface, you’ll find the table of riffs. While the book flows from start to finish, each riff is individually numbered and includes a snapshot of Key Topics and a unique QR code that supports easy referencing and quick sharing. The Foreword from Brad Feld and the book’s Introduction prepares you for what to expect and then we dive in! The Table of Riffs below is your first look at the modern circus that’ll energize whatever you’re building. After the book becomes a new favorite, we end with the book’s closing matter. Readers can refill their mug even more in the About The Author pages, meet the 21 contributing authors, acknowledge those who brought this book to life, sneak backstage for people interested in writing a book or book marketing, play in a mini crossword puzzle, and explore more timeless resources to keep us all building… TOGETHER.

PART ONE: ENTREPRENEURSHIP

1. Uncharted
2. Early Moves
3. Maverick
4. First in Line
5. Ideaworks
6. Pain Relievers vs. Vitamins
7. Minerva
8. Prismatic
9. Fresh Powder (cc)
10. Escorting Execution
11. Slow & Fast
12. Triangulation
13. Real Skills
14. Ship It
15. Storytelling
16. Super Sentence
17. Isochronal
18. Sequencing
19. Feedback Is Data
20. Down Under (cc)
21. Slide Deck Design
22. Attention Traps
23. Captive
24. Momentum Mountain
25. Fructifying Fortitude
26. Shifting Gears
27. Echoes
28. Breakout Valuation
29. Head Start (cc)
30. Not to Lose
31. Landing
32. Voices (cc)
33. Diplomacy Disrupted (cc)

PART TWO: LEADERSHIP

34. Listen
35. Jargon vs. Understanding
36. Small Business Owners
37. ArtOfficial (cc)
38. Linchpin
39. Significance
40. Permeability
41. Everyday Activism (cc)
42. Generosity Builds Trust
43. Atmospheric
44. Winds of Outrage
45. Executionist
46. Import Knowledge
47. Líneas Invisibles (cc)
48. Interested Introductions (cc)
49. Overtime
50. Decisions
51. Aphorism
52. Airport Foot Massage
53. Enchanting Events
54. Reluctance
55. Collide
56. Playforce (cc)
57. Playforce Principles
58. Adaptability (cc)
59. Adapttitude (cc)
60. Extra Credit (cc)
61. Tenured & Tired
62. Seasonality
63. Linear
64. Diversified Career Portfolio
65. Visualizing Variety
66. Hiatus

PART THREE: TECHNOLOGY

67. Pure Wonder
68. Innovation Curves
69. Tinker
70. Wireframing
71. Hybridize
72. Time Trappers
73. Cyberspace
74. Producing a Podcast
75. Dollowers
76. Welcome to Web3
77. Mechanized Money (cc)
78. Woven Worlds (cc)
79. Phygital
80. Munch Munch
81. Septenary
82. Conversationalized
83. Yin-Yang
84. Bridges to Tomorrow
85. Digitized Consciousness
86. Replicants
87. Incentivized Reality (cc)
88. Propulsive
89. Neon Future

PART FOUR: LIFE & HAPPINESS

90. Open to Next
91. Indexing
92. Uncertainty
93. Anticipation
94. Recursion
95. Horizons
96. Anxiety
97. Creation vs. Consumption (cc)
98. Waiting Rooms (cc)
99. 1% Better
100. Training Wheels
101. Bloop
102. Winterizing
103. Santa Is Real
104. Front & Center
105. Pebbles
106. Goodnight Moon
107. Totality
108. 13.8 Billion
109. Dark Matter
110. Gimmies
111. Hole-In-One (cc)
112. Serendipitist
113. Bookmarks
114. Feng Shui
115. Sedona Sands
116. Love Letters
117. One & Only
118. Wayfinders
119. Winding Whys
120. Oversubscribed
121. Intrinsic
122. Conspicuous Kindness
123. Sharing
124. Endowment
125. Perpetuity

For more details or to consider creative ways to collaborate, download the book summary, grab a book, and connect with the author to talk through more ideas.

By Ben McDougal, ago

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.

LISTEN on APPLE PODCASTS
LISTEN on SPOTIFY

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