What I learned building an accelerator from scratch

Lessons on scaling operations at a startup

Hayley Caddes
10 min readJan 22, 2021

About 18 months ago, I decided to take a leap of faith.

I went from a lead data scientist at a brand strategy firm to being a director of a human accelerator for Gen Z entrepreneurs — The Knowledge Society (TKS).

By human accelerator, I mean that instead of trying to find and develop the next SpaceX, we try to find and develop the next Elon Musk.

I serendipitously stumbled upon the opportunity to join TKS to help build the TKS New York program from scratch with Mike Schmidt (founder and CEO of Dovetale). Despite having no prior experience building anything remotely like this program, I followed my gut and took the job.

A lack of experience leads to an excess of learnings, almost all of which can be useful to anyone building or scaling startup operations from scratch. I’m writing this series of articles in the hopes that people will find what I learned valuable and widely applicable.

First, I’ll focus on what it takes to build a successful accelerator from the ground up.

My next two articles will focus on how to develop the superpowers of high potential people and on how to make the vision for a community’s culture into a reality.

Real quick: I want to give a HUGE thank you to Mike, all my coworkers running programs in other cities, and the founders of TKS. They all contributed significantly to my personal growth and the success of TKS as a whole. The insights in these articles were gleaned because of their guidance, support, and incredible hard work 🙏

Okay first, WTH is TKS? 🚀

High school students join TKS to learn how to use emerging technologies to solve the world’s biggest problems.

TKS consists of self-directed project-based learning, unique opportunities to solve real-world problems for billion-dollar companies, skill development such as writing and presenting, access to top-tier mentors, and mindset training all within a global community.

Our approach in TKS NY was to build the “gold standard” for scaling TKS to other cities. We pursued this task with the mindset of “how can we make NY the best program in the organization?”

Spoiler alert — it worked. I’ve distilled my insights into five main factors that contributed most to the success of myself as a director and therefore the success of the TKS NY program. They are as follows:

  1. Ability to spot high potential people (in 15 min)
  2. Questioning the status quo
  3. Building solutions that scale
  4. Understanding how to communicate value with different stakeholders
  5. Combining executive presence with emotional intelligence

🔑 Success Factor #1:

Ability to spot high potential people (in 15 min)

People and culture exist long before the product.

The application and interview process for TKS is modeled after that of Y Combinator. If a student makes it past the written application stage, we get to know them in an interview that lasts no more than 15 minutes.

Through interviewing hundreds of students, I learned that if you can’t efficiently read between the lines, you can’t identify raw talent.

To spot high potential people in under 15 min, I find out:

  1. What excites them? → What is your current obsession? Why does that fascinate you? (Look for their eyes to light up)
  2. Do they think differently than the people around them? → What’s something you believe to be true that your parents (or friends) would disagree with you on? (A modified version of the famous Peter Thiel question)
  3. Are they naturally curious? → Have you taught yourself anything outside the confines of your classes recently? How do you motivate yourself to learn something new?
  4. Are they self-aware? → You say you’re passionate about solving [X]…so why is it that you haven’t solved it yet? What holds you back from doing [Y]? If you could build your own best friend, what traits or qualities would you give them?
  5. Are they open-minded/coachable? → Is there an experience that fundamentally changed the way you think about yourself or the world? Did anyone influence that experience?
  6. Do they have intellectual horsepower? → Teach me something about [insert whatever they said they’re passionate about]. Describe to me as if I’m a 3-year-old how [X] works. How do you figure something out that you don’t understand?

Red flags would include the inability to think deeply about the answers or the inability to work hard at — or be curious about — anything outside of the realm of what they need to do for school or to get into college. If you’re talking to adults, then outside of their normal job or routine.

Me after talking to a 15-year-old about space manufacturing.

🔑 Success Factor #2:

Questioning the status quo

To build the “model” city for scaling TKS, it was my job to identify inefficient processes that don’t make sense quickly and then iterate on solutions.

First-principles thinking is the best mental model to understand the “why” behind the way things are done. It helps leaders identify holes in their logic, and it helps me identify patterns of thinking within an organization.

Here’s my process for questioning the way things are done and bringing up pain points to founders:

  1. Be objective — recap how it’s done now, along with the upstream and downstream effects.
  2. Present the problem as an “area of opportunity,” rather than framing it as “this is what’s wrong with your process.”
  3. Do the research. When diagnosing a problem, it’s most important to identify bottlenecks, opportunities for automation, and pain points for different stakeholders (i.e. directors, students, parents).
  4. Come prepared with three suggested solutions based on data or past experience solving a similar problem. Help the person to whom you’re giving feedback visualize what the solutions might look like.
  5. Make it collaborative. Ask for feedback on your ideas, and make sure people feel like the brainstorming process was a group effort.
  6. Be clear on the outcome and metrics of success — if we do this, what will it look like and how will we know it was successful? Who will own this and execute it?

It is critical to have high attention to detail and relentlessly pursue understanding the first principles behind all existing processes, programming, and frameworks.

🔑 Success Factor #3:

Building solutions that scale

I primarily use three mental models to generate solutions to 10x the program and evaluate their scalability:

80/20 Rule:

  • Also known as the Pareto Principle, this mental model was formalized by Italian engineer who noticed that 80% of Italy’s land was owned by about 20% of its population.
  • In this context, 80% of your results come from 20% of your effort.
  • To identify opportunities that 10x the quality and scalability of the program first I decide on the metrics for what success looks like, and then I figure out the lowest effort, highest impact way to get there.

Inversion Thinking:

  • It’s the process of working backwards to solve a problem, rather than forwards. Charlie Munger advocates using this mental model to avoid stupidity, rather than seek brilliance.
  • When I am building or modifying something for the program, I think about what would create the opposite result of what I want.
  • Before making a decision, I ask, “If this failed, why would it have failed?” This is also a useful tool to preemptively identify and put out fires before they start.

Ocam’s Razor:

  • The simplest solution is preferable to one that is more complex.
  • This mental model 10x’d my ability to efficiently and quickly solve problems or develop new programs. The simplest solutions are the easiest to execute, test, and iterate.
  • You can always build up from starting simple, and using this mental model is ideal for making initial conclusions before the full scope of information can be obtained.

Side note: to build processes and solutions that scale, I am meticulous about documenting everything. I document the desired impact, metrics of success, plan of action, ultimate outcome, and areas of future improvement.

🔑 Key Success Factor #4:

Understanding how to communicate value to different stakeholders

The 3 different groups I have to convince of the value of participating in TKS are:

  • Students
  • Parents
  • Partners — CEOs, entrepreneurs, engineers, scientists, investors, etc. that sponsor projects, provide mentorship, or give fireside chats to the students

My simple — but not always easy — framework👇

Show that you genuinely care about the person — and how your program/product will make them feel — with enthusiasm!!

Show stakeholders that you’re looking out for their best interests and that you’re willing to go above and beyond to add value to their lives. Do that enthusiastically, and the system is fool-proof.

This is how I convinced companies like LEGO, Illumina, and Barclays Center to do mini McKinsey-like consulting challenges with the students.

We framed these challenges as an opportunity to have a bunch of smart, technical teenagers work on some of their biggest problems — for free. We made it clear that we deeply cared about the students adding value to these companies. We would be actively involved in the entire process to ensure that the students delivered high-standards recommendations.

Plus, the companies get marketing material showing them supporting a STEM program and giving high schoolers a unique opportunity. As a bonus, they would feel good about themselves. Always crucial to frame an ask as a win-win-win.

Using this same approach, we were able to convince Evan Spiegel to give the NY program a private fireside chat. We made it clear that it would be low effort for him, but high impact for the students. Conveying how much we cared about the impact he would make on the students was key.

Not-so-humble brag — we recently found out he still keeps this photo we sent to him on his desk 😎

As for communicating value to the students, the key thing we realized was that most of them have never had an adult enthusiastically care about pushing them to grow in a way that doesn’t relate to grades or college. To convince them of the value of the program, I show them that I genuinely care about pushing them to reach their own goals.

I consistently show them that I care about their growth by giving them constructive feedback, helping them build relationships, sending them random articles about something they’re interested in, and giving them intros from my network. My job is to be their number one fan.

🔑 Key Success Factor #5:

Combining executive presence + emotional intelligence

To interact with people, build a brand, and develop important partnerships, one thing young people are always told to do is develop their executive presence — that certain je ne sais quoi channeled by the most powerful people in the world.

When looking for good examples of executive presence, I found that one specific type of executive presence is glorified, especially in the tech world. It looks like the guy who is a stoic, direct, somewhat harsh, hyper-productive, modern-day oracle with a touch of arrogance masqueraded as intellectual horsepower and thought leadership.

Female execs are often coached to come off as more masculine because of this. No shade — alright, maybe some shade — but I definitely don’t fit into that box.

Actual footage of me trying to be a Stoic

Instead, I built better relationships and was a better coach to the students when I simply put an executive spin on my authentic self, a tactic I learned by observing Sara Blakely.

I started to lean into my natural enthusiasm, high-energy, tendency to talk a little too fast, creativity, and, most importantly, the emotional intelligence I’ve invested a lot of energy into developing over the last decade.

And you know what??

I grew more as a leader in just a few months than I had in the years I spent trying to mimic people whose personalities don’t resonate with my own.

The key to being an effective coach and gaining access to unique opportunities for the students was to combine executive presence with emotional intelligence.

In my experience, it’s a superpower to be able to combine executive gravitas with an ability to empathize and connect with people. It’s clear to me that the success of your employees (my students), and therefore the success of your company (TKS NY), hinges on your ability to do this.

All of this comes down to your ability to Figure Sh*t Out (and Get Sh*t Done)

The foundation of all of these insights is channeling a “Figure It Out” mindset on a daily basis and executing efficiently. This comes down to 1) knowing what your resources are, both in terms of tools and people, and knowing how to use them effectively, and 2) creating feedback loops.

Intentional feedback loops, coupled with a high level of confidence in my ability to figure stuff out, is the reason I was able to build TKS in a brand new city from scratch without previous experience doing anything remotely similar.

Ultimately, if you want to push people (or a program, or a company) to grow outside of their comfort zone, you sure as hell better be willing to step outside of your own.

Check back for my next two articles in this series on how to develop the superpowers of high potential people and on how to make your vision for your community’s culture into a reality.

--

--