Startup Weekend: Still my favorite event

For a long time, hackathons were my pastime.

What's a hackathon?

Basically, an event where the objective is to build and launch a new product or business in 1-2 days.

So, while others spent their weekend doing things like sports and art, I spent mine coming up with business ideas and trying to make them a reality.

Then, in mid-2016, I joined a startup. And I couldn't set aside weekends to go to hackathons anymore.

(Actually, I did manage to squeeze one into 2017.)

Between work and COVID shutting down in-person events, I haven't been to a hackathon since.

Well, this past weekend I broke that streak.

Startup Weekend

About a month ago, I was thrilled to learn that my favorite hackathon, Startup Weekend, was scheduled to happen in the nearby city of San Salvador, Jujuy.

Startup Weekend is an event where participants:

1. Gather on Friday night
2. Pick business ideas and form teams around them
3. Refine the business idea and try to launch it during the weekend
4. Pitch the results of the work on Sunday evening

I was even more excited when I convinced my wife to participate, too. She'd have a chance to share in an experience that's given me so many valuable to learnings and memories.

I've written about my experience at Startup Weekend before.

But, this was my 17th Startup Weekend. And, the first after a 7 years gap.

So, I felt like it was worth reflecting on.

The experience

One of the reasons I wanted to write about this particular experiences is because it was a unique one for me.

It's the first Startup Weekend I've been to that wasn't in English.

Startup Weekend generally kicks off with people lining up to give 60-second pitches for new businesses they'd like to create.

Over time, I've gotten pretty comfortable doing quick idea pitches.

But, this was the first time I had to do it in Spanish.

In fact, it was the first time I'd spoken in front of any audience in Spanish.

So, I was pretty nervous.

Would I be able to finds the words to describe my idea?

Would people understand my accent?

Well, I got past my fear. And, I'm pretty sure at least like 80% of the people understood my accent.

So, that was a big win for me, even in just the first hours of the event. ✅

My wife pitched an idea too. Like me, she was nervous. But, more because she'd never pitched a business idea to a crowd at all.

Regardless, she did it and presented like pro.

Her idea ended up getting the 2nd most number of votes when everyone chose which ideas they were most interested in working on.

So, it was turned turned into one of the official project for the weekend.

From there, she formed a team. Then, led the team through the process of developing the idea and pitching it to a panel of judges Sunday night.

(I had the luck of being allowed onto the team. 😉)

Startup Weekend, across cultures

This event was a great opportunity to see Startup Weekend in action in a country and culture different from the one I grew up in.

Amazing thing: It brought out all the same passion and excitement I've seen at every Startup Weekend.

That was what I'd expected. But, it's one thing to expect it and another experience it first-hand.

As always, I:

1. Met awesome people
2. Learned new things
3. Grew from the process of trying to accomplish something challenging in a short time

I also saw something I've never seen in any hackathon, work environment, or elsewhere.

Two teammates worked 100% from their mobile phones.

They did research, website design, and created our pitch deck.

And the quality they delivered was beyond what most people deliver on a full laptop.

It blew my mind.

If you'd told me a week ago was I was going to witness, I'd have told you I'll believe it when I see it.

Well, now I've seen it.

New lessons

Here're a couple key take-aways for me.

A couple of them're things I've noticed before, but still need to improve on.

A couple are new insights.

1. Cut corners and get the job done

I have perfectionist tendencies. This slows me down when I need to be moving fast.

I think that over time, I've gotten better at tuning it up and down. But, it remains a challenge for me.

There were numerous points during the event where I realized I was obsessing over details and made myself let go.

But, the moment that stands out the most is a point where my wife asked me, "why don't you use a no-code tool?"

Honestly, the idea hadn't occurred to me.

It was like a splash of cold water that brought me to my senses.

Here I was, struggling with an unfamiliar technology that kept breaking.

Once I'd started down that path, I began obsessing over fixing the issues with the technology instead of whether I was using the best technology for the job that needed to be done.

I lost perspective on the most important thing. Which was simply to deliver something sufficient to demonstrate the concept.

My wife's insight saved me from failing to deliver.

2. Don't take your experience for granted; be patient with others

There're a couple key lessons that form core of what Startup Weekend teaches us.

These're things like validating assumptions, identifying problems before building solutions, etc.

I've spent so much time thinking about and practicing these that they've come to feel natural.

Which makes it important for me to remember the mental toll I paid to practice these new ways of thinking.

And, to be aware that others around me may be paying that mental toll now.

So, when it feels like the team's talking in circles, it's likely not with the intent to disagree.

It's more likely the act of processing these new ways of thinking.

3. Sometimes, your area of deepest expertise isn't where your attention's needed

I was the only person on the team with substantial technical experience.

So, that's where I focused my energy.

After some initial team conversations set our direction, I went into my own little bubble to focus on setting up the foundations of the tech we'd need to demo the concept.

I thought the rest of the team would work through any blockers they ran into and continually identify a path forward.

But on the morning of the final day of the event, I found that the rest of the team was frustrated and stuck on a couple issues they couldn't get past.

Tensions were high and they weren't having fun.

I felt a sense of obligation to deliver in the area where I have specialized knowledge. But, I also realized at that point that it wasn't the most valuable contribution I could make to the team.

The most valuable thing I could do at that moment was to reintegrate into team discussions.

So, I closed my laptop recognizing that there was a high probability I wouldn't deliver what I'd originally promised.

On one hand, I felt like I was letting the team down. On the other, I felt like something else was more important.

4. When it comes to human decisions, sometimes you'll never know if you did the right thing

I don't know if separating myself out from the team was the wrong thing to do.

The main reason for doing it was that the biggest source of my own learning was struggling through the process.

I wanted to let the team have their own experience and fully capture the value it creates.

But, I don't know if separating myself out from the team was the right thing to do, either.

Maybe I could've helped make the experience less stressful without taking away from the benefit.

Either way, in the end, team was elated, proud, and eager to participate in future events.

So, things worked out.

But, I'll never know whether some alternative set of choices would've led to more ideal short and long-term outcomes.

I have to live with never knowing whether I did the right thing.

5. When faced with uncertainty, we latch onto whatever we can make sense of

At one point, a teammate was very, very insistent on coming up with a detailed and precise list of costs for the business.

Multiple mentors gave feedback that the numbers were variable and estimates should be reasonable, not precise.

But, the response was, "yeah, but how much does X cost?"

It occurred to me that this's a form of what's known as "bike shedding".

That is, when faced with complexity, we tend to spend excess time on the parts that make sense to us, but aren't very important.

Business models are loaded with complexity and uncertainty.

So, it's natural to want to spend time on parts that're easy to make sense of (like costs), even though they might not be the most important thing at the moment.

If your team's bike shedding, what do you do?

Do you fight to convince them the issue they're obsessing over isn't important?

At some point, that just becomes as much of a waste of time as the bike shedding itself.

I find it can be more productive to just help them arrive at an answer they're happy with as quickly as possible. Then, move on.

6. Even if you know all the details, it doesn't mean you'll present them well

After re-joining discussions about the business model, I built up an understanding of it in my head.

I knew who the customers were, I had a very clear picture of the problems they faced, and I understood what value we could provide them.

I knew how we could deliver that value and ways we could make money in doing so.

Each team member took turns pitching the business to mentors who stopped by our workspace.

When my turn came, I thought it'd be a breeze.

But while making the pitch, I quickly realized I was rambling.

I was talking and talking and using way more words than necessary to get the point across. And, I lost the attention of the audience in the process.

I realized that despite the information being all there in my head, it didn't come out in the well-organized manner I'd have liked it to.

Presenting an idea effectively requires organization and practice. No matter how well you know the material.

7. ChatGPT is an amazing sidekick

As mentioned, I continually ran into blockers with the technology I was working with.

It was frustrating.

But, I was also amazed by how fast I was able to resolve them with help from ChatGPT.

Most of the time, ChatGPT didn't have the solution. But working with it got me there _at least_ 2-3 times faster than reading technical documentaiton and researching via Google.

Modern tech allows a single person to move at shocking speeds. _Especially_, when dealing with unfamiliar technologies.

Productivity gains for AI aren't years out. They're here today.

It's only going to accelerate from here.

Old lessons

Some learnings show up on repeat at Startup Weekend events.

And, as expected, they showed up in full force at this one.

1. Recognize assumptions:

Sometimes, we believe something because it feels correct. Other times, we believe something because we have substantial concrete evidence supporting it. It's critical to differentiate these two situations. The less concrete evidence we have, the higher the risk of being wrong. If we build a business on an incorrect assumption, the odds of the business failing are very high. We increase the odds of success by recognizing which beliefs are based on feeling and seeking concrete evidence to validate those beliefs. Each time we determine a belief was incorrect and we modify it to more accurately reflect reality, we increase the likelihood that our project succeeds.

2. Prioritize the biggest risk:

Businesses are made up of a variety of interacting parts. So when we create a new one, we start out with a lot of assumptions. Each assumption carries risk to the business's success. Some assumptions are more important to the business than others. The more important an assumption, the more risk it poses to the business's success. Since our time and resources are limited, we need to make sure to prioritize working on whatever risk is biggest at any given moment. If we spend time working on lower-risk items, there's a good chance that time ends up having being wasted when a higher-risk item forces us to change direction.

3. Verify there's a problem that needs solving:

Businesses are built on an exchange of value. Businesses solve a problem for customers and, in exchange, customers give businesses money. So, to create a new business, we first need to find a customer: Someone with an problem painful enough that they're willing to pay us to solve it. Whether or not customers exist is the biggest risk we face when creating a new business. So, the most important thing we can do to increase our chances of success is go out and verify assumptions we have about the customer.

4. Interviews over surveys:

The process of creating a new business is: assume -> gather information -> revise assumptions -> repeat. Since it's an iterative, exploratory process, one of our best tools for information gathering is interviewing candidate customers. It's natural to want to use surveys instead of interviews because they let us avoid the emotional labor of talking to strangers (and possible rejection). But, surveys are made up of a fixed set of questions. They're rigid. Interviews, on the other hand, are flexible. They allow us to modify the questions we ask based on what a person's told us so far. So, at when creating a new business, a well-run interview will give us much more useful information than a well-run survey.

5. Know the difference between delivering value and delivering a solution:

Delivering value means resolving a customer's problem. A solution is the way in which that value's delivered. There're lots of ways to deliver value. Each way has its strengths and weaknesses. In everyday life, we're used to buying goods and services that have years of development behind them. It's easy to overlook that when a person has an unsolved problem, they often just want any solution that solves the problem. They don't need something that has years of development behind it. When creating a new business, one of our scarcest resources is time. So, we minimize risk by choosing a solution that solves the problem, but takes minimal time to develop. The solution'll probably be ugly. But it's only worth spending time and money on making it beautiful if we're able to concretely verify that customers need that from us.

6. The process follows an undefined path:

When creating a new business, we're performing a process that involves constant modification of direction. By definition, the path we'll end up traveling is unknown at the start. That uncertainty often creates emotional stress. But, it doesn't have to. When we recognize the nature of the process, we become more emotionally resilient. It helps to avoid becoming fixated on arriving at some destination defined by initial assumptions. It's much less stressful to focus on just figuring out what the next step should be, based on what we learned up to this point. In the end, it's the journey that's rewarding rather than arriving at some specific destination.

7. You don't have to do exactly what people tell you to:

Just like we don't know where our journey will take us, others don't either. At events like Startup Weekend, we get bombarded with information and people telling us we need to do one thing or another. I can't count the number of times I've seen authoritative figures, like mentors, give conflicting advice. The first says "go left", while the second says "go right". Then a third comes along and disorients you by convincing you that you need to forget left and right and think about up and down instead. If we rigidly adhere to what they tell us, we'll constantly end up back at zero, never making progress. It's critical for us to recognize that advice is opinion. Remember that we're the ones talking with candidate customers. We're the ones becoming experts on our business. Advice is tremendously useful, but we have to evaluate whether it helps us progress or throws us into a tailspin.

8. It's only a weekend:

It won't feel like it, but the stakes at Startup Weekend are extremely low. The first night of the event gets us excited as we meet new people, share ideas, and form teams to compete with one another. But, don't forget that when the event's over and Monday rolls around, we all go back to our regular lives. The stress of preparing a pitch for Sunday will be gone. The arguments between teammates will be gone. The mental pressure of thinking in a way we're not used to will be gone. So, try not to stress. Try not to take things personally when there's disagreement on the team. Focus on learning something new, making new friends, and having fun. Of course, when Monday rolls around, hopefully you not only leave the stressful stuff behind, but also carry the good stuff forward. New friends, new ways to thinking, etc. You might find that your life's a little before than it was before you participated in the event.

9. Judging doesn't make your concept good or bad:

Another thing that happens over and over in these events is that we all become focused on "winning". We follow a checklist for what the judges are looking for and forget that we're really there to learn how to create a new business. Having event "winners" is just a tool to motivate participants. I'm on the fence of whether it causes more harm than good. Either way, it's in everyone's best interest to remember that feedback from judges is neither validation or invalidation of your business idea. It's feedback. Just like with mentors and other authority figures, it's something to consider. If you really believe there's a business opportunity, what matters is that you're able to continue runnning the entrepreneurial process. Winners of Startup Weekend _almost never_ continue on to build a business. But, lots of people who don't win the event go on to build functional businesses. It feels good to "win" and it feels bad to not win. But, try not to give whatever situation you find yourself in too much of your emotional energy.

Just for fun

While working on this post, I made a list of all the hackathon projects I could recall working on over the years.

Here're a few of them:

• (2012) Civic Rally: A web app enabling local communities to publicize and collaborate on local projects.
• (2013) TimeTravelFM: A physical radio with a dial to change the era of the music played.
• (2014) French75: A mobile app to purchase and schedule in-home manicures.
• (2015) Push-to-rent: A web app making it easy to find and apply for affordable housing.
• (2016) CSV-to-API: A web service that makes the data from spreadsheets accessible to any app.
• (2017) BabyBooks: An app to that generates age-appropriate books for young children.
• (2024) EvenTesoro: An app that makes it easy to find local events and ensures you never miss one you'd regret missing.