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
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
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
30. Not to Lose
31. Landing
32. Voices
33. Diplomacy Disrupted

PART TWO: LEADERSHIP

34. Listen
35. Jargon vs. Understanding
36. Small Business Owners
37. ArtOfficial
38. Linchpin
39. Significance
40. Permeability
41. Everyday Activism
42. Generosity Builds Trust
43. Atmospheric
44. Winds of Outrage
45. Executionist
46. Import Knowledge
47. Líneas Invisibles
48. Interested Introductions
49. Overtime
50. Decisions
51. Aphorism
52. Airport Foot Massage
53. Enchanting Events
54. Reluctance
55. Collide
56. Playforce
57. Playforce Principles
58. Adaptability
59. Adapttitude
60. Extra Credit
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
78. Woven Worlds
79. Phygital
80. Munch Munch
81. Septenary
82. Conversationalized
83. Yin-Yang
84. Bridges to Tomorrow
85. Digitized Consciousness
86. Replicants
87. Incentivized Reality
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
98. Waiting Rooms
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
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

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 interactions, 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 riff’s QR code to find our special business model canvas. The areas are numbered to curate multiple canvases that each highlight one 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.
  1. Value Propositions – What value do you plan to deliver?
  1. Channels – Where can you connect with this customer?
  1. Customer Relationships – Who are you working with and how can you make this customer feel appreciated?
  1. Revenue Streams – What are all the ways to earn income?
  1. Key Activities – What actions ensure this customer cares?
  1. Key Resources – What is needed to keep building, and how might needs change to maintain momentum over time?
  1. Key Partners – Who can help to make this story sustainable?
  1. Cost Structure – What costs go into activating this customer segment, and how is pricing organized to support realistic profit margins that align with a healthy financial model?

By telling the story of how you’re creating value for one customer segment, hypotheses are 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.

 

ORIGINAL POST

The New Year is already starting to feel like old news, eh. Let’s shake off that early temptation to push your new idea toward someday. Look, I get it. There was intoxicating enthusiasm when you first thought through everything over the holidays. As you’ve returned to routine, the idea that felt like it was the one & only thing that mattered, now seems to be falling down your priority list.

Extra Shot

This is normal, but we’re not normal!
We are the weird who make a ruckus.

After some creative wireframing, I challenge you to setup (at least) two meeting to breath life into this budding idea. First, meet with a #givefirst mentor. This should feel like a supportive space, but avoid rainbows and butterflies. Be realistic by sharing the exciting aspects of the idea, but also the challenges. As discussed in YDNTB, a fast 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 this energizing form of curiosity uncover new understandings. Pivots are inevitable and this exploration adds confidence as the original ideal 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. Your actually protecting your personal bandwidth by not swinging at a bad pitch too many times. Be smart to optimize these early interactions. 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 absorb reality into the idea. Show up, stand out, follow up, stay connected by accelerating their work, and let’s keep building.

To do so, let’s continue brewing into this month’s theme of early moves. The business model canvas is a tool for crafting a story that sells. Here is a business model canvas that includes a little extra encouragement.

As we dive in, I’d like to share a suggested cadence from a friend of mine. Based in Sacramento, JDM is a fellow founder, entrepreneurial ecosystem builder, and tenacious content creator. He will be sharing a caffeinated contribution soon, but the way he moves through the business model canvas caught my attention. In short, most business models can’t be told in one story so it’s not one box at a time, but one story at a time. Instead of trying to boil the ocean, organize different stories for each customer segment. I’ve numbered each box in this downloadable business model canvas as a friendly guide.

  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 – Based on this single customer, outline the value you’ll deliver.
  3. Channels – Where will your business connect with this specific customer?
  4. Customer Relationships – Who are you working with and how will collaboration feel?
  5. Revenue Streams – Based on the first four boxes, what’s the exchange the value?
  6. Key Activities – To deliver on the promise, you must execute with action(s).
  7. Key Resources – Using all seven capitals, here’s what’s needed to keep building.
  8. Key Partners – We can do more with less in the connected era. Who helps you get where?
  9. Cost Structure – The financial capital needed to go from problem to solution.

By telling the story of how you’re creating value for one customer segment, hypotheses connect through all nine boxes and are properly contextualized. Now add more stories, one at a time. To stay organized, use a clean business model canvas for each customer. With different stories told for each customer, color code each story as they are merged into one business model canvas. As everything blends together, the rainbow of color creates a roadmap to reality.

By Ben McDougal, ago

Voices

the streets are restless
voices low,
rumbling of those
who feel forgotten
who feel the die was cast
before they were even born.

they hunger for the chance
to make something their own
to etch their mark in the wall of the world.

and in the shadows,
small fires are being lit
not by kings or queens
but by ordinary hands
with ordinary dreams.

it begins like a forest rising
out of swamp and tangle
messy, alive, unpredictable—
where strangers meet
where trust grows in broken soil
where one seed
can seed a thousand.

it says:
no one will save us
except us.

it says:
the right to begin
is the right to belong.

and if enough of us answer,
if enough of us care,
then out of the discontent
out of the silence of the left behind
will rise
a chorus of builders
a rainforest of possibility
a people remaking the world
with extraordinary love.

Extra Shot

This poem is from Victor W. Hwang.

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

Líneas Invisibles

Están por todos lados. Este barrio contra el otro. Nuestra comunidad contra la de ellos. Mi estado contra tu estado. Este país contra aquel país. Las líneas invisibles crean lealtades. Crean un sentido de pertenencia. Ayudan a estructurar los recursos. Pero con el tiempo, también pueden crear barreras, divisiones y frenar la colaboración.

DOSIS EXTRA

Esta enriquecedora contribución fue escrita por Jorge Sánchez. Este generoso traductor une a líderes angloparlantes e hispanohablantes de todo el mundo.

Los buenos líderes reconocen la importancia de pertenecer, pero también comprenden que el futuro se construye sobre puentes, no con muros. La innovación no se limita a nuestro lugar de residencia, lo que nos invita a celebrar la singularidad de cada ciudad, región, estado y país, mientras abrimos la puerta a la colaboración entre diferentes culturas. Esto se ve desafiado por el contexto histórico compartido entre dos lugares. Cuando las personas de una comunidad tienen opiniones preconcebidas sobre otra, estas suposiciones pueden limitar el interés en la colaboración futura. En lugar de repetir quejas del pasado o lamentarse por lo que le falta a la propia comunidad, reconozcamos lo que sí tenemos. Celebremos la singularidad que aporta una diversidad enriquecedora y avancemos gracias a la colaboración con nuestros vecinos.

Además de la colaboración comunitaria, se requiere un esfuerzo adicional para desarrollar negocios a través de fronteras invisibles. Siempre habrá factores específicos a considerar, pero aquí presentamos algunas actividades clave para construir puentes entre diferentes lugares.

  • Participa y comparte experiencias en ambos entornos.
  • Encuentra un aliado honesto que comprenda las diferencias culturales.
  • Crea una red de contactos en ambos lugares y únelas.
  • Estructura legalmente un negocio para ambos entornos.
  • Mantén al día licencias, permisos, obligaciones fiscales, impuestos aplicables y auditorías.

El lugar de origen aporta valor cultural a cualquier situación, pero esto no tiene por qué convertirse en una limitación. Aprender a desenvolverse en múltiples entornos permite acceder a mejores recursos y ayuda a que las zonas vecinas prosperen sin perder su propia identidad. Respetar las fronteras invisibles es necesario, pero la verdadera oportunidad, los recursos y la armonía esperan a quienes construyen juntos.


ENGLISH VERSION

They exist all around us. This side of town versus that side. Our community versus that other community. My state versus your state. This country versus that country. Invisible lines create loyalties. They create a sense of belonging. They help structure resources. Over time, they can also create silos, divisions, and limit collaboration.

EXTRA SHOT
This contribution was written by Jorge Sanchez. This translator unites English and Spanish-speaking leaders worldwide.

Leaders recognize the importance of belonging, but also understand that the future is built on bridges, not walls. Innovation is not restricted to where we live, which calls us to celebrate the uniqueness of individual cities, regions, states, and countries, while also inviting collaboration between different cultures. This is challenged by the historical context shared between two locations. When people in one community have opinions of another community, assumptions can limit interest in future collaboration. Instead of relaying ongoing complaints stuck in the past or dwelling on what your own community lacks, recognize what you do have. Celebrate the uniqueness that adds healthy diversity and go further thanks to a neighbor who can extend progress.

Along with collaboration at a community level, extra work is required for individuals building a business through invisible lines. There will always be specific environmental factors to consider, but here are key activities to build on any border.

  • Show up and share stories in both environments.
  • Find an honest ally to understand cultural distinctions
  • Build a network in both locations, then unite them
  • Legally structure a business to span both environments
  • Maintain required licenses, permits, financial variations, applicable taxes, and ongoing auditing

Where you’re from adds cultural value to any situation, but this does not need to become a limitation. Learning to inhabit multiple environments enables people to access better resources and helps neighboring areas thrive without losing their own identity. Respecting invisible lines is necessary, but authentic opportunity, resources, and harmony awaits those who build together.

By Ben McDougal, ago