Entrepreneurs Are People, Too
Five Ideas for Creating Transformative Founder-First Experiences
From 2011 to 2019, Blackbox Connect brought more than 400 founder/CEOs from across the globe to live, learn, and grow together. We pioneered an immersive, founder-first approach to startup acceleration, allowing force multipliers from across the globe the opportunity to connect with role models, experts, and one another in the heart of Silicon Valley.
This was grounded in a belief that by elevating entrepreneurs themselves — their mindset, purpose, vision, and leadership — we could strengthen their abilities to grow great companies and to play significant and positive roles in the success of their home startup ecosystems.
I’ve witnessed first-hand how powerful the approach we developed can be in helping entrepreneurs to access their highest potential — many times, while in the process of running experiments that helped us to solidify how we thought about our approach, I and my team would find ourselves blown away by what could happen when we got the conditions just right. It felt like magic.
As I celebrate an incredible growth chapter of my career at Blackbox, I’d like to offer up my learnings around how to build experiences that put founders and their human experience at the center of supporting business growth. This is by no means exhaustive, and is offered humbly in the hopes that there is some helpful nugget here for those who share my love of working with entrepreneurs (or leaders of any kind).
First things first! What doth make a founder-focused experience? These special experiences are characterized by the fact that they:
- Recognize the critical role a founder’s development plays in the ability of their startup to create and maintain a competitive advantage
- Place special focus on the founder’s unique role within the company, elevating their ability to think critically and lead dynamically across key areas like strategy, vision, culture, team, fundraising & investor relations, positioning, and storytelling
- Support entrepreneur-led ecosystem growth by empowering founders to take on leadership roles in shaping their home startup communities
- Complement technically-focused programs by addressing a gap in support for the human element of entrepreneurship, offering a more holistic opportunity to serve founders, startups, and ecosystems
Sounds pretty good, right? But designing something that ticks each of these boxes is challenging and nuanced and, in many ways, is a nascent concept in the startup world.
I’ve landed on five key learnings around how selection, immersion, culture, content, and community impact a great founder-focused experience, which I’ll share here.
1. The people are the experience
The mark of a great experience is one that depends on its participants in order to come to life and create real meaning. I listened to a podcast recently where Benja Juster outlined the four components of experiences — the physical, social, creative, and spiritual — that tap into fundamental human needs. While you can design the optimal conditions for these needs to be met, the caliber of the container you create is largely dependent on who enters it.
One of the most fascinating parts of Blackbox Connect is how extensively each program cycle was shaped by the individual founders selected, as well as how they came together to form a collective as unique as a fingerprint.
The most important considerations we optimized for in selecting Blackboxers were diverse perspectives, growth mindset, and force multiplier potential.
In a founder-focused experience, every person has something to offer and full participation is a necessity. Therefore, diversity isn’t a “nice to have” — it’s a must. Selecting a group that represents a range of genders, ages, ethnicities, creeds, skills, interests, experience levels, and personality types creates a textured and transformative learning environment. This allows founders to challenge their assumptions, access new feedback and perspectives, and exchange valuable knowledge and insights. Diversity can also disrupt the natural tendency towards competitiveness that is often present startup communities, but must be overcome in order to lay the foundation for a container of trust, vulnerability, and authenticity.
There are loads of smart, capable entrepreneurs in the world. But finding those with a true growth mindset — meaning they’re curious about understanding themselves and others in order to grow — is more rare. While controlling for a certain level of company readiness/viability is important (and dependent on the objective of the program or event), it’s just the first step. Identifying entrepreneurs who are willing to face hard truths, challenge themselves and their assumptions, and give and receive thoughtful feedback is a pre-requisite for a high-quality founder-focused experience.
Silicon Valley was built by force multipliers — those who were not only able to accomplish gargantuan feats themselves, but who used their success to champion others and build the infrastructure for the next generation of leaders. At Blackbox, we sought to scale our impact through empowering those with force multiplier potential. Identifying this potential has a lot to do with asking local partners, investors, and fellow entrepreneurs about those founders who have shown promise not only as leaders of exciting companies addressing a real market lead, but as early architects of their startup ecosystem. It also involves placing a focus on an entrepreneur’s ideas for how they’d like to contribute to their home ecosystem throughout the interview and application process. Who, if given a boost to increase their chances of success, will most positively impact their community via mentorship, investment, and other forms of leadership along the way?
2. Immersion is the foundation of transformation
Entrepreneurs are immersed in the day-to-day reality of running their companies — managing teams and deadlines, holding meetings, updating investors, and putting out fires. As facilitators of founder-focused experiences, our task is to create an equally immersive environment, and in so doing, offer the space for participants to reset, refresh, and recommit to the challenging and exciting path before them.
When someone is immersed in an experience, they feel more able to take risks, to challenge existing assumptions, and to be open to new perspectives and ideas. Deep learning requires leaving your comfort zone, and convincing people to leave their comfort zone requires them to feel psychologically safe and supported.
Over the past eight years, Blackbox Connect has seen many iterations of setting. In the early days, founders came to quintessential “hacker house” in Atherton, pitching their companies by the pool at investor barbecues. Next was a bed & breakfast at a Palo Alto inn. Eventually, the operation moved to the heart of San Francisco, taking over two different historic mansions (first the Archbishop’s Mansion and most recently, Taohaus) to bring global entrepreneurs under one roof to experience the energy of Silicon Valley.
The common thread has always been a recognition that space matters. A lot. No one wants to immerse in a space that doesn’t make them feel great. Our goal is to offer a space that creates delight and eliminates friction around the simple stuff — healthy snacks, quiet & comfortable bedrooms, top-notch hospitality — so that founders can focus on challenging themselves where it counts.
In running these two-week residential programs, I became partial to live-in experiences — they uniquely accelerate bonding, allow for deep after-hours learning, place everyone on even ground regardless of background, age, or experience level, and encourage an ownership mentality — but immersion can take many forms.
A founder-focused environment should have the following characteristics:
- Comfortable (does it make them feel at ease?)
- Inspiring (does it evoke creativity, fun, and beauty? Is there a cultural or historical context at play?)
- Informal (can they be candid and authentic here?)
- Collaborative (are there physical spaces for co-creation?)
- Dynamic (are there a variety of spaces for different modes or activities — indoor, outdoor, quiet, collaborative?)
Beyond the physical environment where an immersion takes place are important programmatic and experiential considerations.
Entrepreneurs are heroes: the men and women in the arena pitting themselves against all manner of uncertainty and strife. In designing opportunities for their exponential learning and growth, we should place equal or greater focus on the beats of the hero’s journey than on the final destination.
What does this mean? Firstly, that no detail is too small. From seemingly mundane considerations like well-timed breaks and healthy snack options, to balancing the intensity and volume of information being shared, to larger programmatic themes that form the emotional arch of an experience, great founder-focused programs and events weave everything together to create the conditions that set up individuals and the collective for success.
In planning each cycle of Blackbox Connect, we always started with the beats or themes that make up the arch of the experience — from there, we booked speakers, planned workshops, balanced the flow and cadence of the agenda, and so on.
One of the most rewarding lessons I’ve learned during my time at Blackbox is around the power of rituals. Mackenzie Hall, our resident founder mindfulness expert, and Carson Linforth Bowley and Ting Kelly of Ritual Studio taught my team and I how from rethinking daily habits to creating a profound sense of communion, rituals are an invitation to be more intentional in the way we live and connect with the world around us.
In the context of our two-week program, we used simple daily rituals like starting each morning by taking ten deep breaths or a minute of silence together before going around the room to do a “gut check” of how each person was feeling to give everyone a chance to fully arrive and connect before launching into the day’s schedule. We also use rituals at the end of the program to initiate Blackboxers into the wider global network.
We’ve found that this deepens the immersive experience and invites participants to commit to its co-creation each day. Rituals can also help an experience to be anchored in a respect for holistic wellness (physical exercise, healthy eating and sleeping habits, decompression, mindfulness and mental health, etc), which often takes a back seat to other demands on a founder’s time and attention. It’s important that these are accessible enough to be immediately beneficial for founders, and offer a simple but powerful takeaway to begin implementing with teams upon their return home.
3. A strong culture invites magic to emerge
We talk a lot about culture in the context of helping founders craft it more intentionally within their companies, but a strong cohort (or group) culture is also essential in creating a transformative experience to which everyone buys in fully. So what does that experience look like?
Our “picture of success” in designing Blackbox Connect was to maximize the possibility for the following to take place:
- Founder-to-Founder Learning & Coaching
- Immersion, Introspection, & Experimentation
- Intentional Serendipity
- An Opportunity to “Reset, Reenergize, & Recommit”
- Leveraging the Group IQ/EQ/PQ (Potential Quotient)
- Honest, Constructive Feedback from Diverse Perspectives
- Bias Toward Action & Iteration
After many years of programs, during which a distinct cohort culture always emerged organically, we learned that certain basic conditions increased the odds of the above happening — asking everyone to be present (meaning physically there and putting away phones/laptops during sessions), insisting on confidentiality, being mindful of conversational turn-taking, etc — but that there was also an exciting opportunity to invite founders to affirm and contribute to our picture of success, and then to decide what conditions would be necessary to get there.
We started facilitating an exercise on Day 1 of each program in which we asked “How might we create the conditions for success?” This led to a process of brainstorming behaviors that would make the experience we wanted to create possible. The top behaviors selected by the group would then form the basis of the cohort culture over the next two weeks and beyond.
This had a remarkable effect on the way Blackboxers adopted an ownership mindset in buying in to a clear set of expectations to which they consistently and enthusiastically held themselves and each other accountable.
It was of paramount importance to us to create an environment that encouraged authenticity, vulnerability, and participation. Otherwise, we understood that founders would stay where they were comfortable, navigating only surface-level issues rather than taking real risks, and their growth would be incremental vs. exponential. Creating this type of environment requires fostering a deep level of trust.
We created and reinforced trust through a series of positive feedback loops. Before founders even arrived in San Francisco, they noticed something different about our application process — we wanted to dive deep on their personal motivations for starting their companies, the interpersonal challenges they encountered with their cofounders, team members, and investors, their fears and doubts, and their visions for the future. On Day 1 of each program, we dedicated ample time to letting Blackboxers get to know each other as people before even introducing their startups. We asked everyone to adopt a coach mentality and highlighted not only their challenge areas, but where their talents or experiences could help others, then built in opportunities for them to do so.
We also reinforced it through our behaviors. Culture is reinforced not by values alone, but how those values manifest as behaviors. Our team was mindful of opportunities to demonstrate vulnerability ourselves, transparent when we didn’t know the answer, and insistent upon creating openings for founders to co-create their experience. We also were extremely conscious of the speakers and mentors we platformed. Talented, successful people are a dime a dozen in Silicon Valley — we did our best to only invite people in who embodied humility, self-awareness, and honesty. If these people are role models, it matters what behaviors they’re modeling.
4. Learning is dynamic & interactive
An experience that aims to help founders scale themselves alongside their companies should offer programmatic content that supports critical thinking, leadership, awareness of strengths and vulnerabilities, authentic “big picture” storytelling, and strategic decision-making.
Learning and growth opportunities should come from a range of sources and be available in a variety of formats, always with an invitation for interaction and real-time feedback.
Entrepreneurs never cease to amaze me in their ability to exchange wisdom across sectors, geographic contexts, and experience levels. Our job as facilitators is to create the container and the right balance of structure for this exchange to take place, then to get out of the way.
Sometimes I’d get excited when planning a program and pack the schedule with brilliant speakers, only to realize that maximizing opportunities for peer learning and reflection was in many ways the biggest value add for founders. While expert speakers bring wisdom and inspiration to the table, their expertise should be balanced with the “right now” shared experience that founders desperately seek from one another, especially in parts of the world where the startup ecosystem is not yet robust.
What are the levers most uniquely under a founder’s control that influence their chances of success?
In working with hundreds of founders across a wide array of sectors, stages, backgrounds, and cultural/geographic contexts, we chose to place special focus on the following topics because we feel they are universally critical for founding teams to get right:
- Leadership at the Intersection of Culture & Strategy (What winning looks like, how you win, understanding culture as an integral part of how you win)
- Team Building and Scaling (Founder equity & ESOP, building teams at different growth stages, hiring/firing, org design)
- Storytelling (Entrepreneurs must build the storytelling muscle in order to better understand their own motivations and rally support behind their vision for the future)
- Design & Customer Empathy (Building a customer-oriented culture from the beginning, designing for the customer journey)
Blackbox has leveraged a vast network of over 400 successful entrepreneurs, top-tier investors, subject matter experts, coaches, and opinion leaders to connect global founders to sources of deep knowledge and inspiration. I’ve often been asked how we motivate these people to share their time, insights, and personal networks with us — do we pay them? (The answer is no.)
Convincing busy, highly-successful people to be part of something like Blackbox Connect is about feeding their souls, not their wallets. Speakers like Adam Cheyer, Mike Maples, Michelle Zatlyn, and Julia Hartz met with our founders year after year because they aligned with our mission, we created a special and memorable experience for them that they couldn’t access elsewhere, and we clearly communicated the impact that their investment of time had on the lives and companies of Blackboxers.
Furthermore, we’ve taken care to water our garden over time. Strong networks are about relationships, and thinking non-transactionally to connect dots and create value for people and the things they care about.
5. Communities need a shared sense of purpose
Perhaps the driving force behind the Blackbox approach to startup acceleration has been a commitment to elevate entrepreneurs as heroes in their own journey and to platform them as leaders in their markets and communities. We’ve aimed to support a type of entrepreneur-led ecosystem growth that offers a viable, inclusive alternative to attempts to create carbon copies of Silicon Valley in every corner of the globe.
We’ve found it incredibly important to create a clear, compelling sense of identity and purpose around what it means to be a part of a worldwide community of values-aligned founders, focusing not only on the benefits, but the responsibilities of being a Blackboxer.
In recent years, we asked founders to take a pledge to seal their initiation into the alumni community:
The impact has been real — over 40% of Blackboxers came through the program by way of nomination from an alum. In places like Ireland, Pakistan, Spain, and Brazil, where a critical mass of Blackboxers exist, we hear stories from local partners about their effect on the ecosystem:
“I have watched with amazement as you have transformed several of our founders into confident entrepreneurs who have gone on to scale their operations and contribute to our ecosystem. Even now I watch several of them training the next generation of entrepreneurs. This ‘pay it forward’ and ‘giving back’ process is wonderful to see. The networks they have created with global founders they met during your program is something that will continue to provide support and friendship as they continue on their entrepreneurial journey.”
- The people are the experience — select those with diverse perspectives, a growth mindset, and force multiplier potential
- Immersion is the foundation of transformation — the space matters, as does designing for the arch of the experience and using rituals to invite presence, participation, and holistic wellness
- A strong culture invites magic to emerge — collaborate with participants on your picture of success and the behaviors needed to get there
- Learning is dynamic & interactive — balance opportunities for peer learning with a founder-specific curriculum and a diverse set of expert speakers & mentors
- Communities need a shared sense of purpose — offer alumni the chance to be part of something global and impactful, focusing on both responsibilities and benefits
Was this helpful to you? You can dive deeper with the full playbook version here.
If you’re interested in designing experiences, programs, or initiatives that level up leaders of any kind, I’d love to hear form you. Shoot me a note at firstname.lastname@example.org or connect with me on LinkedIn.
While I’m no longer with Blackbox in a formal capacity, I remain enthusiastic about the organization’s future. Stay up to date with what’s next here.