The MIT Global Entrepreneur’s Bootcamp — Part 4

Or, the time five people from five continents pitched at MIT (read Part 3)

The astute among you will realise that this picture is taken looking west

Tuesday 9th August

It’s a truly beautiful morning, warm and glowing with a bright summer morning radiance. It’s hard to begrudge getting up on days like this, even after two and a half hours sleep. Despite it being 6.30am there are people walking purposefully to work and I realise that I’m starting to enjoy my commute to the MIT Sloan building. I’m now in the habit of grabbing an apple and a cup of coffee from the hotel as I leave the deserted foyer; I’m too early to even see the famous Kendall Hotel buffet being prepared.

The team are a bit low energy at 7am — something I can understand as I look at our uninspiring problems on the board and the broad topic we were left with last night. The mood soon begins to pick up when we decide to let the process decide whether the idea is good or not. I’m certainly guilty of not really loving the problem of ‘sustaining healthy relationships’, but I realise that it’s common to be in a position where you don’t have the privilege of loving the idea you’re working on. I decide to commit to the problem as if I loved it.

I’m pretty sure I’m not alone in my ambivalence, but we’re buoyed by each other’s company and agree that the chance of having an idea we all love and that would pass the 24 steps is infinitesimally small. In addition the initial market research that they team managed in the small hours of the morning is reasonably promising. Most people we have spoken to have a significant romantic relationship and (fortunately) many of those are committed to making it work in the long term. Perhaps this shouldn’t be surprising, but it’s given us a first taste of broaching the difficult topic of relationships with people outside the friendly walls of the classroom.

Breakfast with a legend

Not all legends are for every audience — for some it’s sporting heroes or politicians — but in some circles, particularly the database-loving web developers who were coding in the late nineties, Philip Greenspun is a big deal. For a small number of us in the audience who learned to build data driven websites from Philip’s books, we may well owe at least a chunk of our income to the man teaching for the next hour.

Philip is delightfully refreshing to listen to, as anti-establishment as his reputation and the anarchic chaos of the early web would have us believe. He talks animatedly about the perils of doing business with venture capitalists and the reality of the mid-level managers you’ll be left with when the A-team have convinced you to allow them to invest. In his typical style, he advises us to only work with venture capitalists when they’re coming to you and never when you need them. It’s the sort of contradictory advice that makes sense when you squint.

Bill Aulet follows on from Philip at 9.45am. He talks about unit economics, financials and the reasons not to attend trade shows. He advises, particularly, against letting engineers staff trade show stands, especially if there’s a chance they’ll be asked how something works. Not only will they happily explain exactly how the thing works, but the person asking will invariably be a competitor.

Some other gems from Bill’s session this morning include trying to ensure that you don’t need humans in your sales process (“they get expensive very quickly”), always giving ranges rather than falsely accurate predictions and stressing to us that “the best customer is the one you have.”

At 11.30 we officially break for lunch, but the team keep on with the market segmentation work we’ve been struggling with. It’s confusing and tough to segment a consumer audience, especially when our problem is as broad as ‘improving relationship health’. We struggle to come up with a vision of what we need to produce, even breaking out the Disciplined Entrepreneurship chapter to give us a steer on what we’re doing. Lunch is over, and we’ve missed the food — not for the last time.

Ministry of Supply, IDEO and a vision

At noon Aman Advani, an alumni and founder of Ministry of Supply steps up to address the class to talk about startup operations. One of my key takeouts from the session is how they addressed the challenge of hiring — swapping from an initial focus on individual ability to a test of team fit. One of the ways that they brought this into their culture was to change the interview process — their first interview is now over coffee, lunch or a beer with both the hiring manager and someone unrelated to the role to prevent the selection coming back to expected job performance. It’s an interesting tactic, and something I file away for later.

There’s a quick coffee break, and our team takes the time between lectures to come up with an initial draft vision statement. We end up with, “We help people invest in their relationships”. We’re thinking something like a Fitbit for relationship health, much like the actual Fitbit is for physical health. This plan ties nicely with one of Jose’s ideas to develop a bracelet or smart band to keep people in touch with their partners even over long distances, by transmitting touch through the band. It’s a neat idea that we know Jose has the skill to build, but we’re not sure if people will buy it. At least now we have a product idea, a vision and something to actually test with users.


It’s no secret that I’m a big fan of design thinking, a phrase that is now very much in vogue following its popularisation by Tim Brown at IDEO. For me, design thinking and lean philosophies are two sides of the same coin, focusing on customers, value and rapid iterations. I’m thrilled when Prof. Steven Eppinger takes the floor at 1.15pm and I’m feeling particularly smug as he introduces design thinking, claiming that he and Elaine have been teaching it for many years, just without the buzzwords. I couldn’t agree more.

Steven tells us that he’s going to talk about IDEO and their famous appearance on ABC Nightline (well worth watching if you haven’t seen it before). IDEO are one of the first design companies to merge design and engineering and there’s an astonishing amount to take from the video as we dissect it in the class — how they approach problems, how they work as a team, how their culture and hierarchy impacts their delivery methods and how they interact with clients.

The elevator pitch from hell

At 4.30pm there’s a break, and then time set aside for the teams. Officially we’re supposed to be preparing a demo elevator pitch for our mentor, but as we’ve not spoken to many real users yet, we decide to get out on the streets with the intention to rack up fifty user interviews. We fall short but rack up nearly thirty interviews, which is giving us more confidence that people, especially those who are in, or have been in, long distance relationships would like the ability to stay more in touch with their partner.

We come back to the class and start preparing for our elevator pitch. There’s a fair amount of confusion about what format the pitch will take. Our initial assumption was that it would be a one minute pitch to all the other teams. We turn out to be quite wrong as we watch two of our regular agitators and tormentors for the week, Billy and Marius building an impromptu elevator out of boxes and furniture. It’s going to be a roleplay and Marius and Billy will be joined by the wonderful Chi-Chu Tschang to play the role of evil VCs.

We start to prepare, addressing our discomfort with the pitching by all taking turns doing rapid fire, sixty second pitches, over and over for 45 minutes. Everyone in the team gets many attempts at developing their own script, and the constant repetition and ad-libbing produces some great moments which we’re confident will play well with the audience. We’re having the most fun of the course so far, each round of pitching to our own fake VCs outdoing the previous one. We learn that Elisha does an excellent impression of a Kenyan, which is perhaps natural as he’s Kenyan. Passing mentors and other members of the class keep stopping by to see why we’re laughing so much. We’re confident that we’re going to nail it and feel like the team is really starting to perform.

It didn’t feel this much fun when it was happening. Look at their cold, dead eyes. Like sharks.

All the teams then gather for their round with Marius, Chi-Chu and Billy. We get selected last, and it goes absolutely to hell. Whether intentional or not, the mentors brutalise us. I’ve won the chance to speak after our constant practice and lose the script heroically. The evil VCs in the elevator literally shut me down with a stare and I get barely a sentence out in the minute we have. Our plot twists and theatrics are all off cue and fail to land. We’re so awful — scratch that, I’m so awful — we get a second chance in the makeshift elevator and it’s worse than the first. Our carefully scripted comedy is on the floor in tatters around our feet and we look totally unprepared and shambolic. I feel utterly responsible for this cataclysmic failure, and that I’ve deeply let the team down.

Crestfallen doesn’t even begin to describe how I feel. The feedback is harsh, and rightly so. Despite all our preparation, we choked in the moment. I console myself with the fact that I’ve learned more from this feedback than if we’d landed every line and sailed through to rampant applause. I also learn just how strong the team is — while it’s pretty obvious that I dropped the ball, at no point did I feel anything but support from the people I’d let down. We all shoulder the blame of the catastrophic failure, but it’s a stark reminder of how tough Friday will be.

And so, we decide on an idea

We move on from the disastrous elevator pitch quickly, going back to our boards and setting an aggressive goal to progress from our market segmentation work through to defining the high level product spec by the end of the night. We start refining the market segment down to those with long hours, people working away from home, people with variable and shifting or antisocial hours and students separated at different colleges. We’re still not at the point where we’ve really got a clear product or end user, but we’re starting to whittle down the field.

Elisha demonstrates the Kenyan version of Eensy Weensy Spider to Jose and I

As the evening runs out a major pivot approaches and we don’t see it coming. The best moments of creativity have been where random ideas collide and we wander off randomly to chase them for a while. Earlier, we’d spent about an hour laughing continuously at an idea to reinvent the flush toilet with something that encouraged 50% of the population not to pee on the seat.

Underneath the (literally) unsanitary problem was a fascinating social engineering challenge which we decided in the end to abandon because it was just too large, and we lacked the engineering talent to deliver in a week. The energy in this session had started to attract the attention of people around us like Luciano, who becomes something of an unofficial godfather to the group as our energy picked up over the remaining days. It’s obvious that these bursts of laughter and wildness are when our most interesting work is done, and when we encourage the best out of ourselves and the people around us.

Going back to our relationship idea, we’re conscious that the team are still making do with the solution we have. Jose, as an electrical engineer and developer, hasn’t really jumped on the solutions we talk about. At the moment, our idea revolves around a smartphone app that will allow couples to communicate privately, perhaps by chat or voice, collecting data and suggesting reminders — “Hey, you’ve not bought your girlfriend a present in four days” — or performing basic feel good functions like letting the other partner know when you’ve reached a safe check-in zone (for the men in the audience, this is those times when it’s 2am and you’ve become incapable of using your phone to let your wife know you’re not in a ditch somewhere).

I’m conscious that we need to spend time investigating Jose’s original ideas for connected, Internet of Things devices that will be a more interesting technical challenge for him, and we consider this in the context of communication and connectedness between couples. We start to discuss the product concepts which we now need to put in front of end users to get feedback on.

We keep considering the physical devices we could build — a watch or band to add to the app. This approach would give both Elisha and Jose a good challenge to work on, that we’d definitely be able to deliver.

As we traipse into the small hours of the morning, the crazier ideas are starting to get thrown at the wall. Both Paul and Czarina have variously mentioned the idea of a fluffy toy which could be gifted between couples, which has developed from a simple bear to more of an animatronic avatar. Naturally, the fluffy toy has to vibrate.

And this is the part of the story where my mother wishes she’d not sent this article to her friends. Sorry mum. I did warn you.

Here’s where our glorious, unanticipated pivot happens. As we’re talking about, and laughing at, the concept of a vibrating stuffed toy like teenagers, we all know that there’s something we’re refusing to directly acknowledge out loud. We’re avoiding the elephant in the room — the stuffed animal is a proxy for us directly addressing the idea of sex toys for couples.

It’s fascinating to think back to this discussion. We variously flip from serious discussion to howls of laughter. Erdin and Hyungsoo, working long into the night at a table next to our team, are trying hard not to be distracted by the noise, but occasionally shoot us amused glances.

As we talk more, the giggling starts to fade away as the novelty wears off and the conversation becomes more serious and thoughtful. The same concept we’ve been addressing from early in our discussions, of intimacy between couples and a continued investment in a healthy relationship, has been noticeably strengthened by the consideration of physical intimacy.

For two of our market segments — long distance couples, and people working long and antisocial hours — physical intimacy can be a significant challenge. There’s a growing acknowledgement in the team that a grown-up, honest and transparent conversation about relationships should include the discussion of sex. This is a huge social taboo, and we’re at once determined to address it and concerned that this isn’t the type of idea that we should be working on. A very simple conversation settles it for us.

“This is MIT, we can’t pitch an internet sex toy”.

“This is MIT, we HAVE to pitch an internet sex toy”.

And so, the decision is made. Suddenly, Jose has a challenging IoT project to work on, while the team have a significant social, emotional, intellectual and moral product offering to consider. This is a design thinking challenge.

As I finish my notes for the day it’s 3.56am and there’s every chance that in two days we’ll be pitching a platform for remote, internet enabled masturbation to a panel of distinguished judges.

We’re pretty sure this hasn’t been done at an MIT bootcamp before, and it’s a long way from what we thought we would come here to do. Life is full of surprises. Bet you didn’t see that coming.

(Continued in Part 5)

This post is dedicated to Marius and Billy, who kicked my arse over my elevator pitch. Feedback is tough, but without it we never improve. Thank you guys.