Enchanting Events

Leaders bring people together. Thoughtful connections happen every day, but organizing a public event takes a concerted effort. Great events deliver on a promise by consciously colliding a diverse mosaic of stakeholders who share premium human time together.

When an experience unites the right audience, events expand and accelerate progress. Before, during, and after an event, the more value someone receives by committing to attend, the more likely they are to return.

Tactical depth for organizing both live and online events are practical sections within You Don’t Need This Book. Revisit the Community chapter of YDNTB for more on building engagement through shared experiences. With that in place, let’s skip downstream.

Polymorphic Sequencing

Organizing an event combines resourcefulness, content creation, attention to detail, and people who care. It’s planning and executing an experience that offers more value than the time required for attendees to show up.

This sounds straightforward and we see others hosting endless events. This constructs an illusion that leads many to think it’s easy. Yes, anyone can do it, but organizing an event rarely happens without struggle. No experience, a lack of organized resources, or not having the channels to create awareness with enough people who care make any new concept a lift to launch. Fortunately, building into something we care about is work that feels like play and our juice is often worth the squeeze.

Extra Shot

Find a reason to build with others.
Like consistency, it’s worth the sacrifice.

Hosting one event can create powerful effects, but treasure awaits those who keep building into a longer sequence of multiple events over time. As momentum grows, an ability to execute becomes more natural. This allows creativity to expand impact, while people, themes, environments, and other events stay connected. As different experiences begin to rhyme, shared appreciation builds trust that caffeinates whatever you care about. This keeps the supply of events steady, but disconnects occur when the demand changes.

Navigating Demand

Anytime we get good at something, it’s helpful when the requirements to be good stay the same. Sticking with what works is swell, but roles drift and what people need can deviate. Cultural shifts are usually slow, which makes it possible for events to stay in-tune longer, with fresh twists that maintain demand and keep attendance consistent.

When the cultural climate changes more suddenly, organizers can get stuck playing the same song too long. Events that only hold on to what’s worked in the past, may get stagnant and can quietly, but quickly lose relevancy.

Take a global pandemic for instance. As our planet emerged from the COVID-19 pandemic in 2023, public events felt different. Years later, they still do. The world had stayed home for an exorbitant amount of time and when people returned to a new normal, the game had changed.

Online-only communication had been normalized within the pandemic and efficiencies were fun at first, but soon got old. Virtual teleportation grew networks, but the high speed of growth led to fragmentation. While remarkable progress was made, online events began to feel hollow and lacked enrollment without the heart of an experience that transcended an agenda. Virtual meetings had set topics, specific attendees, and only certain people leading the discussion. Inquisitive side conversations diminished, which reduced the serendipity that makes everything awesome.

As impassioned engagement began to fade, the effort to activate events became burdensome. Attention dissolved and leaders lost sight of what their audience needed. The smallest moves felt risky, exhaustion set in, and communities fell apart. This unprecedented time reminded us how relationships can survive at a distance, but struggle to thrive without IRL (in real life) interactions.

As this tragic pandemic subsided, everyone was socially out of shape. It was good to be back together in-person, but a jarring reality remained. People had become addicted to productivity, felt safe in isolation, and a new generation of founders had started successful companies without contact during the pandemic. Showing up for anything felt like an unnecessary task, which led to an aura of optionality.

Enthusiasm to get involved was soon harder to find. Life happens and calibrating how we spend time is worthy, but this ethos can easily devolve into an excuse to do less. To hesitate. To say “no” when a “yes” would have led to more adventure. With altered demand, crowds became harder to curate. Many past events returned to unite attendees through a similar experience, but just as many returned to dwindling congregations that felt stagnant. Failed events led to organizer burnout, which meant less opportunities for good people to collide. Social fracturing on a global scale took time to mend, but as leaders began to explore new ways to bring us together, fresh ideas were collided, formats adapted, new collaboration emerged, and value returned.

A global pandemic is a dramatic example, but when change is constant, how can leaders evolve the supply of events to meet demand for the people in a startup community and the organizations within an entrepreneurial ecosystem?

These cultural crossroads remind us that a beginner’s mindset preserves a willingness to experiment. When the status quo is easy, lean toward what’s hard. Tension can help avoid more dead ends and when challenges are seen as opportunity, adaptive events can meet evolving demand. 

As events transform to fit the moment, remember a why, foster diversity, harmonize with key stakeholders whose needs may have changed, consider the cadence, explore new venues, try new marketing maneuvers, and recommit to local leaders hosting contiguous events.

The lasting promise is that evolving demand does not change the value of serendipity. Unscripted collisions keep us all wild and healthy. Great events spark invaluable intuition and help peers avoid misery. Human ingenuity connects dots, ideas are given space to mingle, progress is seized, and a renewed audience can leverage exponential encounters that are united through a positive-sum mindset.

Parlay Measurements

Systems like the assurance from data and many forms of data can be compiled when it comes to assessing events.

Use traditional metrics that have been helpful, but even small pigeonholes can make good data dirty, so beware of the measurement traps all around you.

If you’re truly interested in enchanting events for those you may never meet, let intuition guide you. Leverage analytics, but don’t let them disguise reality. Instead, parlay good, clean data with feedback from the people who care. Listen to attendees, offer surveys, welcome being wrong, segment attendance trends, find joy with informal check-ins, and don’t limit feedbacks loops to only the loudest in the room.

Attendee feedback, experiential wisdom, and good data supports better understandings. Decisions get easier and there’s less guessing. With success and this state of understanding, program details can evolve in a shared direction and technology can be gamified to support more stakeholders. This level of growth is not for the faint of heart, so don’t be afraid to keep it chill, but if we keep building and handy solutions are made to be easy, user appreciation leads to enrollment. This bolsters good data as fans use it to grow the events they care so much about.

If a decline is clear and nobody cares enough to provide feedback, harder decisions are coming soon. Even if it’s time to graduate gracefully, this type of honest assessment provides confidence that helps us learn, appreciate what was accomplished, and enjoy a closing sunset.

Growth vs. Therapy vs. Entertainment

Developing and attending events is an effective way to add and enhance real skills, but stay cognizant to keep your time and purpose aligned with events and related attendees.

There’s no wrong answers, but there is a difference between events geared for personal growth, versus therapy or entertainment. For example, if you need basic education, but the majority of attendees are there for entertainment, newcomers will feel a sense of fun, but the motionlessness may not have them sticking around. Another example is the welcoming environment that lacks in-depth insight, which will have more experienced people choosing to disengage. These examples remind us that when the messaging does not match the experience or an atmosphere can not support goals of an attendee, less value is felt and impact can fizzle.

To align expectations and the experience, be clear with those you seek to serve. Avoid trying to be everything to everyone, understand the type of people who make your events relevant, and welcome constructive feedback. This intentionality attracts the right attendees, which makes it easier to deliver an experience that resonates. Evolve to meet changing demand, but remain viable by expanding how people feel between numerous events.

Versatility

Expanded viability can be achieved when one event has different flavors or when various leaders host different types of mutually dependent events. Multipurpose events led by one person or organization look better through a short-term lens and often see faster results, but ego, thirst for control, a wrongful sense of ownership, and ulterior motives will always get in the way. A more lasting and sustainable path involves a diverse collection of ecosystem allies who are excited to share an audience between related events. Consistency and variety will keep people coming back, but that’s a heavy lift for one, versus a lighter lift for many. Distribution of events within a startup community adds depth that makes it easier for organizers to be consistent as they focus on what they do best, knowing other events deliver supplementing variety.

As individual attendees experience different types of value in a connected community, engagement grows thanks to versatility that people can get excited about together.

Currency of Attention

There was a time when we didn’t know every option. The Internet and social media changed that. The bombardment of information has literally changed our biology and reduced attention spans with endless options that saturate our lives. When combined with an innate desire for routine, attention becomes currency and is much harder to earn.

When time is precious and attention is scarce, the perceived optionality of events will always keep them on the chopping block. For event organizers trying to fuel awareness, it’s not enough to just open your doors or post an event online.

Leaders must stay ahead of the innovation curves, attend other community events to pave two-way streets, revisit communication tools, keep fresh blood flowing, and make an effort to personally invite the right people at the right time. Even as recognition is earned, don’t be complacent, for the currency of attention never lasts long.

Impermanence

If the message has been received, but people are still not showing up or you’re feeling tired as an attendee, determine if the event is still something to spend time with. If it is, don’t hold back. Host more events until you have enough experiential data to honestly reassess. If you’re participating as an attendee, consider getting more involved.

Hopefully a new level of satisfaction is achieved, but if dots still aren’t connecting, it could be time to move on. This will be emotional, but appreciate the impact that was made and learn from the experience. As we wind something down, personal bandwidth is added, so think about how that can be used to create different types of thickness within your interest in events and their polymorphic sequencing.

As you shift gears, the community and target audience may remain, but time away helps to reexamine reality and find new people to collaborate with. With updated perspectives, and the network effect of more people involved, stay urgent, but remain patient as new opportunities emerge.

Deep-Rooted

What’s long-term in the context of events? It’s not rigid math, but it begins by building one event.  To sequence, have ideas on if/how events may lead to future events.

Consistency over a few events is common and one year is impressive. People and programs that run events a few years provide a healthy jolt, stories that go 5-15+ years are given time to root prolific value. Movements feel like 15-25+ years, which include tons of remarkable events worldwide. Interestingly, religion timelines may be the longest cadence for events in history. Consistency is hard, but adds up quietly when you’re around those you love.

What a cadence to support deep-rooted events? Annual events are massive, bring everyone together, and are so amazing. Quarterly events are less common, but can be absolutely excellent over the years. Series are a cool way to experiment with events, because they allow you to feel success, but avoid the weight of forever. Monthly events are easy and take a good year to grow. A monthly cadence is fantastic and it spawns powerful effects, but it’s the weekly events that have a cadence brewed to connect community.

Extra Shot

What’s the longest you’ve hosted an event?

What event have you attended the longest?

Humans will always crave connection, so whether you’re actively evolving events or looking for the next opportunity, be willing to adapt. Deliver on what’s expected, then delight the right audience with unanticipated value. Even within evolving demand, leaders can eliminate the optionality that looms when the currency of attention is required to show up again and again. Word will spread as people feel heard and the opportunity that events present will forever be optimized with timely purpose and lasting significance.

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
5:15Writing 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
1:23:00Startup 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
1:42:50BEN BOT
1:44:05 – Digitized Consciousness
1:45:12 – Vibe Coding
1:46:45Dinostroids
1:49:40 – Quantified Self
1:54:16 – Biohacking
1:56:30 – AI Notetaking
1:59:55 – Founder’s Interest in Philosophy
2:00:50The Entrepreneur’s Weekly Niche
2:07:10 – Obsession over Passion
2:10:20 – Affinity as an Investor
2:11:35 – Fight to the End
2:11:50The 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
2:24:30You 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

Cartoonist

Nathan T. Wright is an artist. He has origins in the early days of social media, made impact inside corporate marketing, and now illustates remarkable art with drawings, cartoons, murals, and more. Ben and Nathan jam on The Adventures of Fatberg, the early (fun) days of social media, the speeds in-house at a large company, leading a creative process with clients, real skills for studying the arts, and understanding the business of being a full-time artist.

After the break that features a reading of Aphorism, Nathan and Ben dive back in by talking graphic recording at live events, the positive tension of smart cartoons, and extending value by reformatting great content into books. EP90 of YDNTP is an absolute bop – share with a friend!

EXTRA SHOT

Nathan T. Wright is the friend who illustrated the mug that has become part of a brand that is Ben McDougal.

What started as the caffeinated, community-driven cover art for You Don’t Need This Book, now extends through the Roasted Reflections NFT Collection, imprinted phygital clothing, the front of tiny ideabooks, temporary tattoos, a huge neon sign, and of course, the artwork for this timeless podcast! Cheers to this episode and another shared relic that keeps the fun brewing!

LISTEN on APPLE PODCASTS
LISTEN on SPOTIFY

BONUS MATERIALS

https://nathantwright.com

The Adventures of Fatberg

https://etsy.com/shop/ntwillustration

City of Santa Ana FOG Activity Book

Roasted Reflections Break: Aphorism

https://NewYorker.com/latest/cartoons

http://Cartoonist.YouDontNeedThisPodcast.com

https://MainframeStudios.org

EP21 – Pinball Wizards 🎙️ Ben Sinclair

EP44 – Do What You Love 🎙️ Scotty Russell

EP55 – Inextinguishable Light 🎙️ Jim Morgan

EP60 – Goosebumps 🎙️ Nic Roth

http://YouDontNeedThisPodcast.com

https://BenMcDougal.com/NFT

http://BENBOT.ai

By Ben McDougal, ago

Push Through

Alongside a career in finance, Steve Walsh is an investor and wrote Make the 10X Leap to help founders scale. We talk about choosing to push through the storm, raising strategic financial capital, collaborating with investors, signals for when it might be time to scale, and all that goes into writing your first book.

LISTEN on APPLE PODCASTS
LISTEN on SPOTIFY

BONUS MATERIALS

https://BisonEquityGroup.com

http://Push-Through.YouDontNeedThisPodcast.com

Roasted Reflections Break: Winds of Outrage

https://BenMcDougal.com/How-I-Wrote-YDNTB

EP59 – Agents of Change 🎙️ Amner Martinez

EP73 – Care Directly 🎙️ Jon Van De Veer

EP84 – Base Camp 🎙️ Jon Kallen

http://YouDontNeedThisPodcast.com

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