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

Woven Worlds

Culture is woven; technology is built. One accumulates through memory and shared meaning, shaped over time by many hands. The other is designed and assembled with intention. This distinction matters because what is built can be finished, while what is woven never is.

Through stories, symbols, and artifacts, each generation adds new layers to the tapestry of our world. What once took only physical form is increasingly becoming digital, carried forward by the relentless evolution of technology. Yet, once introduced, technology rarely remains confined to its original purpose. It’s folded into the fabric of our world where it’s interpreted and repurposed, becoming part of our society in ways its creators could not fully anticipate. This process is cumulative, not merely additive. New ideas rarely replace what came before; they intertwine with it. Beliefs and practices become entangled across time itself.

EXTRA SHOT
This contribution was written by Will Schneller. This founder is a curious creator who explores how art, technology, and community connect.

At the edge of new frontiers, humans reach for the familiar. We stitch together distancethe gap between the known and unknown with shapes we recognize. Sometimes this instinct serves convenience or efficiency, making new systems easier to adopt. An artwork originating in oil paint is trivial to transfer into a physical print edition, and it’s even easier to make that print digitally available. A ticket to a sporting event that once existed on perforated paper now lives on a handy smartphone app. Your favorite album is no longer confined to the shelf but sits among thousands of other songs on a device in your pocket. Other times, replication is a coping mechanism, a way to translate ideas that feel too abstract, too technical, or difficult to explain.

Even when digital systems begin by imitating familiar physical forms, digital depth quietly emerges beneath the surface. Metadata invisibly flows; hidden traces record not just what something is, but how it came to be, and how it moves through networks. MThe meaning in what we create no longer resides solely in appearance or original intent. It accrues through circulation, reference, and response. As these translations settle into everyday use, they begin to expose possibilities that were never present in their physical counterparts. Constraints loosen and rules get rewritten. Systems that once existed to mirror the familiar start inviting exploration, modification, and play. What follows is not a better copy of the old world, but a space where new behaviors and relationships can unfurl.

While some technological advances are purpose-built to solve specific problems, others become playgrounds. Environments where new primitives can be experimented with and explored. For example, blockchains created the conditions for non-fungible tokens to be born. NFTs (“non-fungible tokens”) are digital assets supported by smart contracts that connect to a blockchain. Each NFT is unique, which allows code to autonomously apply, track, and transfer digital signatures and verifiable ownership. Although each digital artifact may have no exact equivalent, it can still evolve over time. These blockchain-native assets allowed us to apply property rights to digital goods and interact with like-minded individuals without corporate algorithms shaping every connection.

Long before NFTs gained prominence, video games had already been rehearsing some of the same ideas. Virtual worlds established shared rulesets, persistent identities, and digital artifacts whose value emerged through play and social context rather than physical substance. Communities formed around common mechanics, aesthetics, and norms. They assigned meaning to avatars, skins, achievements, and in-game assets that only existed as code yet carried real weight. Traditionally, in-game items are effectively rented, disappearing when servers shut down; blockchain-based ownership proposed permanence, portability, and player-held authority. Once ownership can be represented digitally with credible verification, we give users their own cybernated backpack to store, use, and transfer digital assets. Instead of centralized servers restricting our digital assets, decentralized protocols and web3 layering supports ownership across different platforms. tThe conversation expands beyond art and gaming into everyday artifacts like memberships, credentials, and records that structure daily life.

As these digital-native systems mature, they enable entirely new creative and cultural capabilities. Not merely faster production or broader distribution, but fundamentally different relationships between audiences, creators, and artifacts. One such shift was generative creation. Instead of crafting a single, fixed outcome, creators began defining rule sets; constraints, probabilities, and parameters from which many unique expressions could emerge. Authorship moved upstream from execution to orchestration. One of the earliest and most visible examples was Larva Labs’ CryptoPunks which demonstrated that scarcity and identity could be encoded directly into digital artifacts. Each image was simple, but its meaning was amplified by its inclusion within a fixed set, its history of ownership, and its role as a recognized cultural symbol. Platforms like Art Blocks pushed this idea further by entangling the code powering the generative image algorithms with the cryptographic functions of the blockchain itself to create a symbiotic relationship between process and product. Variation became a feature, not a flaw, and collectors became participants in the moment of creation itself.

Alongside generative art, other projects explored coordination and collective meaning-making through radical simplicity. Jack Butcher’s Checks emerged as social commentary when Twitter (now X) infamously monetized account verification, replacing long-standing signals of notability with a paid badge. More than capturing the cultural moment, Checks leveraged the blockchain architecture itself to create an infinite game of coordination where holders could recombine varying edition sizes to create new outputs, thereby elevating them into collaborators. Another of Butcher’s projects, Opepen, transformed the silhouette of a popular internet-native character, Pepe the Frog, into a gallery-esque system in which constraint became the canvas. Artists across backgrounds and styles imagined thematic sets, each adding a distinct thread to the whole. Through distributed voting, token holders collectively enshrined new works into a permanent collection, shaping the canon set by set. Power did not come from technical complexity or visual detail, but from repetition, shared context, and sustained participation over time. The community drove the narrative.

Taken together, these projects revealed a broader shift. Digital artifacts were no longer static endpoints, but dynamic nodes within living systems. Value emerged not only from aesthetics or novelty, but from process, lineage, and collective engagement. Creation became less about producing objects and more about shaping culture-organizing frameworks within which culture could organize itself. In this way, technology did not replace traditional artistic or cultural practices; it extended them, offering new ways for ideas to propagate, mutate, and endure. But more than offering a new set of tools, technology holds up a mirror, forcing us to confront what we value as our physical and digital lives continue to merge, layer by layer, thread by thread.

When novelty fades and attention moves on, what remains is not spectacle but structure. People return to the tangible, not in rejection of the digital but in search of something that is grounding. Digital slips into quieter roles as infrastructure. This isn’t failure but rhythm, an expression of how new technologies mature over time. Every major technological shift follows the a familiar arc discussed in the upcoming Yin Yang riff. Early breakthroughs ignite curiosity and experimentation, producing rapid growth as possibilities are explored. Along the Often described as an S-curve of a technology’s life cycle, this initial ascent is driven by potential rather than stability. Expectations rise faster than practical understanding. Capital and cultural energy concentrate at the leading edge, amplifying both innovation and excess.

Inevitably, the curve bends and the edges begin to fray. Constraints appear and promises collide with reality. What cannot sustain itself is torn away, giving rise to periods of contraction or disillusionment. These moments are frequently mistaken for failures and become opportunities for skeptics to declare their predictions correct. However, they serve a necessary function. They clear the noise from signals, speculation from utility, and fragile ideas from durable ones. What follows is not a return to obscurity but a slower, steadier climb. The technology re-enters everyday life, quietly embedded into workflows, tools, and habits, often under new branding to shed cultural baggage. It stops demanding attention and begins offering reliability. Value shifts from novelty to usefulness, from expansion to integration. The most enduring systems are no longer those that announce themselves loudly, but those that quietly become indispensable.

Each technology life cycle pulls old threads forward, reweaving the physical and digital into a fabric that grows richer with history. Past experiments inform future structures. Early missteps become knots rather than dead ends, points of tension that strengthen the tapestry. Over time, what once felt disruptive becomes foundational, and the boundary between the new and the familiar dissolves until the cycle begins anew. What remains is not the novelty of the tools themselves, but the patterns of use, meaning, and connection sewn around them. Technologies may be constructed in moments, but their cultural significance is woven slowly through repetition and shared experience. In the long run, progress is measured not by what is built, but by what endures.

By Ben McDougal, ago

Teaching Adaptability

Introduction

In today’s rapidly changing world, adaptability isn’t just a nice-to-have skill, t’s essential for survival and success. But how do we teach young people to adapt when traditional education systems often reward rigidity and conformity? Through my work with Pi515, a Des Moines-based nonprofit focused on STEM education for underserved youth, I’ve learned that adaptability isn’t taught through lectures or worksheets. It’s cultivated through experience, failure, patience, and the willingness to meet each child exactly where they are.

I was raised to not make assumptions. I’m solution-oriented, and because of this, I’ve learned to use data to predict what we should teach students. At the core of what we do is understanding learning, understanding each student, and building solutions that work for their unique circumstances. This chapter explores how hands-on learning, entrepreneurship, and real-world challenges develop the kind of adaptability young people need to thrive.

How Technology Teaches Students to Adapt

When students engage with rapidly changing technology, they enter a world where adaptability isn’t optional. A line of code that worked yesterday might break today. A robot design that seemed perfect on paper fails in practice. A 3D print cracks halfway through. In these moments, students learn that failure isn’t final; it’s feedback.

I remember one particular day in our Python learning class. The students had been preparing for weeks to pitch their projects to a CEO. They’d formed teams, written code, and built presentations. There was one team of only girls, and they were ready. But that day, the day of the pitch, their code stopped working.

In a traditional classroom, this would have been devastating, a failed grade, a missed opportunity. But these young women had something more valuable than working code: they had the best PowerPoint presentation of all the teams. They adapted. They showed up. They demonstrated their understanding, their vision, and their ability to communicate even when the technical piece failed them.

Code doesn’t always work. Sometimes it crashes. Teaching tech allows young people to learn in safe spaces and understand that things sometimes fail, and you have to pick yourself up. Opportunities do come, but when you are prepared, even when challenges arise, you can thrive and show up in other ways.

This is the iterative nature of STEM learning. When the code doesn’t work, you redesign. When the robot fails, you troubleshoot. When the 3D print breaks, you try again. Each failure is a lesson in adaptation, each setback an opportunity to approach the problem differently. Students learn that there are multiple pathways to success, and the ability to pivot is often more valuable than getting it right the first time.

The Unique Adaptability of Underserved Students

Students who face economic instability, navigate new countries, or overcome language barriers already possess remarkable adaptability skills. They’ve had to adapt to survive. The question isn’t whether they can adapt—it’s whether we, as educators, can create environments where those existing skills are recognized, valued, and channeled into educational and economic opportunities.

I have seen young people navigate many challenges, and I have seen them win. One story stays with me. I had a student who got pregnant while she was still in high school. In her culture, her father insisted she should get married. But she needed her education. She had dreams beyond what others expected of her.

Though we teach tech at Pi515, we also teach entrepreneurship. This young woman was able to get her GED, but more importantly, she started a business. Today she is an entrepreneur. But before she got there, she had to do things that were uncomfortable. She tried the nursing field. She explored different pathways. She adapted.

When supporting young people, you have to be patient, and you have to truly take time to know who they are and what their skills are. I knew she was good at braiding hair. I would have her do my hair, and I would pay her. It was a small thing, but it helped her see her skill as valuable.

This experience opened my eyes to systemic barriers that require their own kind of adaptation. I began advocating for braiding hair legislation in Iowa—a bill that would allow women to own braiding shops without going to cosmetology school, because cosmetology schools don’t teach braiding and the license requirements don’t make sense for a skill that doesn’t require cutting or chemicals. I didn’t know when I started that advocacy that it would support young women like her. But that’s the nature of adaptability—you learn, you adjust, you find solutions you didn’t know you were looking for.

Her story illustrates a crucial truth: adaptability isn’t just about bouncing back from failure. It’s about recognizing your skills, even when others don’t see them. It’s about finding paths forward when the traditional routes are blocked. It’s about being uncomfortable and doing it anyway.

Meeting Each Child Where They’re At

Adaptability can’t be taught through a one-size-fits-all curriculum. Each student carries their own story, and it is important to not put them in one box. We must give them a safe space to learn and grow, and we must be willing to adapt our teaching to meet their needs.

This requires adaptability from educators, too. When I say we meet each child where they’re at, I mean we truly assess what they know, what they need, and what’s possible given their circumstances. One student might need help with basic communication skills such as ,,,mhow to send an email, how to understand an email. These might seem like simple exercises, but reading emails, writing emails, understanding what to do with the email, knowing what you need to best respond to it—these are crucial skills.

Another student might be ready for advanced coding or robotics. Another might need entrepreneurship training. Another might need us to recognize that their talent lies somewhere we haven’t looked yet—like braiding hair, or art, or community organizing.

You can’t force kids to be who they can’t be, but it’s important to teach key skills that allow them to thrive. Communication skills, for example, are universally valuable. So is the ability to adapt your approach based on what’s working and what isn’t.

Building Adaptability From the Ground Up

We teach these skills young. And yes, how children learn starts at home. I often encourage parents to allow their children to build real-world capacity through everyday experiences.

Chores teach responsibility and follow-through. When a child commits to a task and sees it through, even when it’s boring or difficult, they’re learning to adapt to necessary but unpleasant realities.

Limited screen time, planned and organized—not random and endless—teaches children that entertainment isn’t constant and that boredom can be productive. Adaptability often means making do with what you have rather than reaching for constant stimulation.

Reading actual books builds attention span, imagination, and comprehension. In a world of quick hits and short videos, the ability to sit with a longer narrative and adapt to its pace is increasingly rare and valuable.

Volunteer opportunities where parents don’t intervene teach confidence and social awareness. When young people have to navigate new situations, work with different kinds of people, and solve problems independently, they develop adaptability muscles.

A part-time job while in school teaches time management, humility, and communication. It’s not a bad idea. Students learn to adapt to workplace expectations, to balance competing demands, and to show up even when they’d rather not.

And don’t underestimate simple things: a walk to the park, unhurried conversation, noticing nature, asking questions. Those quiet moments can add real value to young minds. In silence and slowness, we learn to be present and to adapt to the rhythm of the world rather than demanding the world adapt to us.

Student Ownership and Adaptive Pathways

When students have ownership of their educational pathway, they must adapt constantly. Interests change. Challenges arise. Opportunities emerge. The student who thought they wanted to be a nurse discovers a passion for business. The student who loved robotics finds they’re equally talented at graphic design. The student who struggled with traditional academics thrives in hands-on learning.

This kind of ownership requires a different relationship between educator and student. Rather than dictating a fixed path, we create conditions where students can explore, fail, adjust, and try again. We watch for what lights them up. We notice where they struggle and why. We adapt our support to match their evolving needs.

This is where individualized pathways become essential. When we give students the choice to pursue what interests them—whether that’s coding, 3D printing, entrepreneurship, or something else entirely—we’re teaching them that they have agency. And with agency comes the responsibility to adapt when things don’t go as planned.

Entrepreneurship as Adaptability Training

Perhaps nowhere is adaptability more evident than in entrepreneurship. Starting a business requires constant adjustment. You have an idea, you test it, you get feedback, you pivot. The market shifts. Customers need change. Your initial plan rarely survives contact with reality.

Entrepreneurship education teaches young people to embrace this uncertainty. They learn to see feedback not as criticism but as gold. Good feedback can take you to places you need to go. It shows you what you missed, what you assumed, what needs to change.

Most people are always looking for mentors. Young people need to be mentored, absolutely. But they also need to mentor us adults. They thrive in areas where we struggle. They understand technologies, cultures, and social dynamics that we don’t. The relationship has to be reciprocal. They need to learn from us, but we need to learn from them.

This mutual adaptability—where both mentor and mentee adjust to each other, where both teacher and student learn—creates a dynamic environment where everyone grows. The young woman who became a hair braiding entrepreneur taught me about barriers I hadn’t seen. The girls whose code crashed taught me about resilience I hadn’t expected. Every student I’ve worked with has required me to adapt my assumptions, my methods, and my understanding.

Adaptability as a Lifelong Practice

Adaptability isn’t a skill you master once and then possess forever. It’s a practice, a way of approaching the world with openness rather than rigidity. It requires patience—with yourself, with circumstances, with others. It requires the willingness to be uncomfortable. It requires recognizing that there are multiple paths to any destination and that sometimes the path you’re on needs to change.

Through hands-on STEM learning, entrepreneurship, and individualized pathways, we can create environments where young people—especially those who have been underserved by traditional systems—develop the adaptability they need to thrive in an uncertain world.

We must meet each child where they’re at, not where we wish they were. We must create safe spaces for failure and growth. We must recognize that the skills students need aren’t always found in textbooks. Sometimes they’re found in a makerspace where code crashes. Sometimes they’re found in starting a business when everyone expects you to take a different path. Sometimes they’re found in doing someone’s hair and realizing that skill has value.

Adaptability is about seeing possibilities where others see obstacles. It’s about using data and observation to build solutions rather than making assumptions. It’s about being solution-oriented even when the problems are complex and the answers aren’t clear.

Our young people are capable of remarkable adaptation. Our job is to get out of their way—and to adapt ourselves to support them better.

By Ben McDougal, ago

Conversationalized

Humans have long used technology to communicate with each other. As we’ve taught machines to see, learn, speak, and move, computers were invited into the conversation.

ChatUX is technology that helps computers speak our language, with a conversational experience supported by deep learning and large language models (LLMs). ChatUX makes AI easier to enjoy with a potential for accurate, unbiased, and meaningful interactions. This allows the seven types of AI to be so much more than pointless help desks, deceptive lead generators, misleading content, or fake followers on social media. Instead, the objective is to access endless insight with an ability to translate it effectively.

When upgraded this way, ChatUX bridges trust channels to personalize education, enhance business efficiencies, assist customers with empathy, deliver meaningful mental health therapy, and make past tasks irrelevant, all while parlaying multimodality so anyone can effectively express ideas.

As ChatUX evolves, improvements geared for safety and customizability will keep technology in the conversation.

The freedom of speech is a complex topic, but guardrails that identify certain words or dangerous rhetoric helps to keep everyone safe. Along with responsible policymaking, influence layers help to customize ChatUX. This can add depth to personalize an interaction or provide internal teams a more reliable source of truth.

With technology conversationalized, prompt engineering became a professional field of reconstructing inputs to optimize outputs. The demand for a brand new mode of communication reminds us how real skills are required to remain relevant. Fortunately, when it comes to technology, an increased effort here, often decreases effort there. In this case, learning to communicate with technology may require new resources, but ChatUX bolsters a paradigm shift where access to knowledge becomes pedestrian.

Extra Shot

When the cost of information is zero, willpower becomes a path to wealth.

We prepare our children with communication skills while instilling kindness, honesty, empathy, integrity, and so much more. From the words we use to the interactions we share, positive traits can be ingrained into technology for good.

By Ben McDougal, ago

Adaptability

As leaders prepare others for an unpredictable future, an interest in understanding answers and an eagerness to claim confidence is essential. A vital element to both qualities is an ability to constantly adapt.

When technology makes answers easy to find, adaptability makes the human touch unmistakable and more resilient. As students traverse problem-solving activities, they learn to appreciate what goes into the answer. This leads to deeper understanding and boosts adaptability as assumptions are tested and unplanned obstacles are conquered.

Extra Shot

This contribution was written by Nancy Mwirotsi. She is a leader from Kenya who empowers underserved youth through technology education.

Imagine a young student, standing in front of a packed room to pitch her first startup idea. Something unexpected is bound to happen. When it does, real-time adaptability keeps her calm and her voice grows stronger as the crowd responds to her ability to execute despite the disturbance. Outside the classroom, similar manifestations occur when leaders reward team members who adapt to stay ahead of innovation curves and we all know how unpredictable entrepreneurship is, which makes adaptability an ongoing requirement for founders building without a map.

Adaptability strengthens confidence as we then let students lead. When young people are trusted to take the stage, make decisions, or shape solutions, they begin to own their success and claim a confidence that can’t be taught.

As students claim confidence, adults stop underestimating their capacity. This fosters a two-way exchange for students that see themselves in leaders who motivate them to explore, make mistakes, and yet, always remain valued. A shared interest in how things work can then amplify potential as technology is introduced to create awareness, multiply real skills, and actuate ideas. This experience encourages students to go beyond just using technology to find the easy answer. It elevates those who understand how technology works, which continues to shape courageous innovators that avoid the temptation to be mediocre.

Within the unknowns of constant change, adaptability keeps us curious. Enduring curiosity can then activate initiative supported by real skills and expanded through lifelong learning. Leaders who create environments that help others build proficiency in the dynamic elements of playforce principles, prepare us all for the future of work.

By Ben McDougal, ago