How Techstars Brought Us Together by Tearing Us Apart

Kyle DeTella is the Co-Founder and Developer at (Boulder ’16), a developer platform to build, train and deploy intelligent conversational applications. Previously, Kyle was a Software Engineer at Braintree. @kyledetella


Early last winter, during one of our Sunday night founders syncs, the idea of applying to Techstars was brought up. We went through the requisite steps of discussing the pros and cons, the alternatives, and a fair amount of “what-ifs”. Ultimately, we decided that an accelerator was the right move for our company and that the upcoming Techstars Boulder class would be an ideal fit.


The Decision: Reality Sets In



While the application process itself was what I expected, I came to realize that getting into Techstars represented one of our first goals as a startup. Should we get in, not only would that provide a degree of validation for our product, but it would also prove to be our first win as an early team.

Once we were accepted, a new wave of reality swept over the team. Two of us (including myself) were still full-time employees at another company.

A commitment to Techstars also meant a complete commitment to

I admit, I had my share of concerns about the Techstars program. These concerns were mostly personal and centered around the location. The decision to pack up and leave home for three months to live and work in a city which I had never been was difficult for me. But this was something I had always wanted to be a part of. I knew that success depends on taking risks and moving outside of your comfort zone. As founders, we were already distributed between Chicago, San Francisco, and New York; at least this meant I would not be alone in taking this leap. Despite earlier fragmentation in the decision to do Techstars, it was already uniting us.

Month 1: Slow Down to Speed up



Since I arrived in Boulder after the first week of the program, I missed the introductory retreat and lost out on some prime seating in the office. Regardless, I was impressed with the early camaraderie forming amongst the working teams. We were all working to solve extremely different problems but at the same time facing many similar ones. My goal before the program was clear cut — leave my current job, head to Boulder, and go heads down to build our product. We were warned early that we should not expect to get much work done in the first few weeks of the program. Despite these warnings, I maintained that I would still be able to pull this off. I was dead wrong.

I grew to realize that when they said “slow down to speed up”, they really meant slow down. We were pushed to challenge our assumptions on our approach to our business and also to continue to force ourselves out of our comfort zone. The first few weeks consisted mainly of sessions and meetings on any number of topics from project management to mentorship strategies.

As a team, we felt quite overwhelmed and I worried about being pulled away so often from working on the product. I had such a strong desire to build the product our way and I wasn’t receptive to a lot of the feedback and advice we were receiving.

Across our team, we held different views about the benefits of this barrage of information. All in all, I think we balanced each other out though. Maybe that was the point.

Month 2: Supportive Growth



Once we had “settled in” to the program, it was time for us to resume our movement on the hiring front. We had been conducting interviews in the weeks leading up to the program, but had put that process on hold during our adjustment period. After only a a few weeks into the program, we brought on two engineers and an intern. Adding chaos to chaos seemed like the perfect recipe for success.

As it turns out, hiring at that point was a great decision. We were still early enough in the program and the lifecycle of our company where these hires could help shape our direction. But we also had enough time under our belt to sort out how we wanted to work with a growing team. The Techstars team welcomed our new hires as if they’d been there all along. One of the managing directors even offered to help with finding them a place to stay!

Team growth and culture is close to our hearts as founders. A lot of that stems from previous jobs, but we also saw an opportunity to construct our own framework for building a company that people would love working for. At the end of the day, a job is a contract between an entity and an individual. But, a job should also be symbiotic. Its not to say that I don’t believe in structure, but that it is imperative all members of the team feel they have ownership and a voice to enhance the product. I have seen managers act as though an employee does not have a vested interest in the success of the product. To me, this doesn’t compute — particularly at a startup where the performance of the product has a direct impact on your success as an individual. That is a deeper topic for another day though. Between Techstars’ advice on on boarding, culture, and help with housing the team, we had an easier time growing our company at this early stage.

Month 3: Lofty Goals



Each week during the program, all the companies would assemble for a recap of the previous week and to discuss goals for the upcoming week. We found it difficult to adjust to this weekly cadence. For one, these meetings were on Thursdays, which meant a Monday-Thursday timeframe for goals. Yes, we worked through the weekends and we worked on Fridays, but we still clung to the nuances of a M-F work week. I still don’t know if that was the wrong decision, in many ways I feel it set us up better for post-program life. We also had trouble setting KPIs and OKRs in these meetings given the state of our product. Our platform was immature and evolving at such a rapid pace that it was difficult to plan a day or two ahead, let alone a week.

We missed many of our goals on the technical front but did much better on the business and marketing goals. It was rough to keep missing goals and drink fail juice (literally). But, from these failures a new, larger goal began to emerge. That goal was to get our team into a place where we could begin to operate efficiently enough to start hitting the goals we set.

By the end of the program we were hitting a stride and achieved our final two. Aside from the individuality of the goals, these weekly gatherings served as a social catalyst for the companies in the program. Having these few hours each week gave us all insight into the personalities of our peers and fostered a shared mentality. It felt very much like classmates in school. People formed their own groups and cliques. But, at the end of the day, you all shared the same experience and that meant something.

The program itself ends with the presentation of a demo day pitch. The final weeks were spent focused on nailing this presentation. Since we had hit a stride, we were also building product at a fantastic pace. This pitch was another part of the experience where we underestimated the amount of time and effort required. Building product would have to slow down to accommodate it. However, in the end, I saw it as the final polish on the framework of our product to that point. That realization, made all the nit picking and frustrations worth it.

Post-Program: Reflections



Before leaving Boulder, I took some time to reflect on my experiences and what they meant. I’ll make no bones about it, I did not love being away from home for that long. I think that was the hardest part for me personally. However, I would not change our decision to work away from home. We have talked about this many times. Had the program been in my hometown, we would not have been forced into team building. Bonding is naturally accelerated when four founders live in cramped quarters and have dinners and drinks with their first three employees.

For various reasons, namely: discomfort, unfamiliarity, and truthfully — ego, I didn’t take advantage of the program as much as I should have. As a team, we did much better. But Techstars, is as much of a personal experience as a company experience.


This was originally published on Medium

AKLSW Reflections – By Katherine Yang

Katherine Yang, a high school student, signed up thinking she would merely design a few logos and user interfaces. She muses about how that wasn’t the case.

– Pitch an idea to a room of imposing professionals.
– Deliver impassioned speeches about frustrating a singular bee.
– Force the concepts of Nicki Minaj and Twerking onto others.
– Not get booed off stage for making physics jokes.
– Consume such a volume of coffee in so short a time.
– Drive my vision and lead a startup.
– Carry on despite initially being the only one in my team to show up on the pitch morning.
– Utterly lose my shit.
– Pull it off anyway.

These are all things I didn’t think I’d do but ended up doing in 54 hectic hours.

The above list sure as hell isn’t meant to a step-by-step guide to startup success, either.

Even the most renowned ‘syllabus’ for startup success acknowledges that there is no formula for startup success. The only certain methodology is dependent on a single process:


‘Learning’, after all, is the thing you embarrassingly admit to your boss after having failed.

As a full time learner, I may have been slightly put off by this concept. Generally, being a student means consistent learning and limited doing, and Startup Weekend was meant to be a chance to get off of my haunches to actually do something.

But this ‘validated learning’ is an integral strain particular to startups – which really are just methodical bouts of testing assumptions, failing, flailing and learning.

Eric Ries, pioneer/god of the lean startup movement said of ‘learning’, “We must learn what customers really want, not what they say they want or what we think they should want.”

The distinction between ‘What I think the customers want’ versus ‘What the customers really want’ is probably the most valuable thing I’ve learnt.

Heck, that’s all I know, having signed up with utterly no entrepreneurial basis.

With ‘Customer Validation’ as one of the key tenets of the judging criteria, and as the thing that each of the twelve start-ups scrambled to gather in the 54 hour stretch, my naïve mode of thinking shifted away from an ‘end goal’-centric strategy to one based on creating what people want to buy.

It sounds elementary.

But visionary stubbornness, whether it be based on age or supposed experience, turned out to be a huge detriment to many startups.

Time and time again, glimpses of fraught groups and emotion would escape from the one-minute update pitches and neighbouring tables from conflicting interests.

All from that simple dichotomy – ‘What you think the customers want’ versus ‘What the customers really want’.

If the loftiness of the central idea is crumbling under the weight of undesirability, the only way to stay alive is to pivot.

There are three stages to the ‘pivot’.

The reallocation of resources – every one of us started up with nothing so this should be fairly easy.
The reorientation of the startup’s ethos – now, that’s a bit harder.
The admittance that you were wrong – good luck surviving Startup Weekend if you can’t bear to do that.

And if you pivot fast enough, you may be able to gather angular momentum.

(Because physics jokes.)

Thanks Auckland Startup Weekend crew, my awesome team and mentors of all shapes, ages, and professional backgrounds. You’ve all let me be weird. You’ve all changed my life.

I’ve learnt a lot.