We have an assumption that the winners of pitch competitions are the most prime for venture capital and startup success.

This couldn’t be farther from the truth. I’m going to share two stories on why I believe that.

Years ago, I got “The Email.”

In April 2018, I had applied to pitch in a pitch competition through the FinTech Exchange conference in Chicago. The two-day event was sponsored by BarChart and CME Group. All of the top financial companies and FinTech companies in Chicago would be there.

I had previously received an email that I was not selected to pitch for the competition.

Then, out of the blue, six days before the competition, I received the email below:

WOW!!

I felt pretty jazzed, not only for the opportunity, but for the pitch itself.

Several months prior in late 2017, I had developed an investor pitch that was garnering incredible feedback from investors and audiences around the country. Nearly every audience I pitched for, I would predictably receive numbers of people coming up to me and complimenting me on my pitch. I felt that I was at the height of my pitching career, and this opportunity couldn’t have come at a better time.

My confidence going into that Chicago pitch competition was sky high.

The Pitch Competition Arrives

There were five judges - all from esteemed careers in finance and technology.

There were around 500 people in the audience - investors, corporates, and service providers - from across the spectrum of financial technology.

I was one of 16 startups from across the country. Founders were flying in from all across the country to pitch at this competition - Chattanooga, TN, Denver, CO, Atlanta, GA - and me from Green Bay, Wisconsin.

I scanned the list of the startups and founder who were pitching - I recognized Craig Fuller of FreightWaves, touted as the “Bloomberg of the Supply Chain industry,” a startup that would raise a $13M Series A that Summer 2018 with 8VC leading the round. They have raised over $90 million in VC funding to date, per Crunchbase. Most of the other startups pitching had raised millions of venture funding.

Yet, there I was, a pre-seed FinTech Startup who had just been accepted to the FIS Startup Accelerator that Summer 2018.

I felt like I was a child among giants. Yet, I was incredibly confident that I going to slay Goliath and win this competition because I had a killer pitch.

Because an incredible pitch is all that matters to win a pitch competition. Or, so I thought….

The Moment Arrives

The founders got up to pitch, one after another. In highly technical finance founder-form that I had grown so accustomed to over the years, nearly all of the founders made their companies sound incredibly sophisticated and smart.

Except, I couldn’t understand a thing.

✅ In a pitch, sophisticated does not sell, and copious details do not cut through. ✅

I had grown to see that a pitch could be a startup founder’s secret weapon. It was my secret weapon.

See, I had developed this hypothesis… which continued to be proved correct over and over again every where I pitched. My hypothesis was,

The vast majority of founders’ pitches cannot be adequately understood or are uninspiring.

A pitch has such a short form factor of 5-8 minutes that, at it’s core, a pitch is about leaving an unforgettable first impression.

I figured that I needed a 10x better pitch to win on the first impression level, and then that would set up favorable next steps.

My aim was to optimize for what I saw as the “ROI of being understood.”

That’s how I crafted my pitch.

My Pitch and Delivery

Instead of telling you about my pitch, I’ll show it to you below.

After the pitch, the judges asked questions. Nearly every one of them commented on the quality of my pitch! (I had previously observed that none of them hardly commented on the quality of the other startup’s pitches.)

After the Q&A, even the emcee got up the microphone afterwards and commented, “Wow, that was really great!” 

Got this one in the bag for sure.

The Competition Results

I anxiously awaited the several hours of time when the winners would be announced. Finally, the moment came. The emcee stepped up to the podium.

“In third place… Freight Waves”!

Me, (thinking to myself): “That’s OK, not surprised they’re on the podium. I can’t wait to tell people that I placed above FreightWaves in a pitch competition!”

“In second place… Coinified!”

Me, (thinking to myself): “Well, I guess I’m in first then. I mean I did get really positive feedback from each of the judges, so here we go!”

“And in first place… PanXExchange!”

Me, (thinking to myself): “WHAAATTT!?!”

I couldn’t believe it. All positive signals until that moment.

I had a killer pitch. FIS was just about to invest in our company. We were up to great things.

I was immediately brought low.

After the Event

After the event had concluded, I had many people compliment me on my pitch. In that sequence of 20 minutes, I observed what happened. Opportunities presented themselves that didn’t exist prior to that event.

• Several investors approached me to specifically comment on my pitch, and then asked to set up a meeting with me to discuss our fundraise.

• The emcee came over to me and commented on my pitch, asking if I wanted to be a guest on his podcast, Futures Radio Show. I recorded the episode about eight weeks later.

• Several corporate individuals who I had been trying to reach unsuccessfully, now came up to me and connected with me.

How I Think About Pitch Competitions

After the competitions that I’ve pitched in as a founder and judged as an investor, here is how I now think about pitch competitions.

1. Turn the Exposure of the Competition into an Opportunity

✅ Exposure is the only predictable outcome of a startup pitch competition.

The startup controls how much they turn that exposure into an opportunity. ✅

In a pitch competition, who the winners are only matter in the short-term. Even the monetary prizes are nice but not usually game-changing for execution.

What matters is the long-term network connections and opportunities that the exposure brings. The biggest win that I experienced from the Chicago pitch were those three opportunities above, all seeded by the quality of my pitch. 

A startup cannot control the outcome of the judges deliberation and the competition, but they can choose to make the most of the exposure they are given.

2. Consider the Background of the Judges

In retrospect, right out of the gate, I was at an inherent disadvantage to win that pitch competition.

Consider the five person judging panel that I faced in Chicago’s pitch. All of them were corporate executives, not VC investors. In recalling the experience of each of them, only one of them was familiar with bond trading. Even then, that judge traded derivatives, not the same problem space as the problem we were solving in bond trading.

Think about that. Nearly all of the judges could not appreciate the problem that we were solving in bond trading and how we were solving it. It’s human nature to gravitate to problem sets that are more familiar as you can gauge the impact and value proposition way better.

Furthermore, who the judges are in any pitch competition varies drastically. Depending on each individual judge’s experience and context, the experience of the judging panel may range from individuals that hear startup pitches all the time (like me or another VC), to those that spend minutes to hours reviewing company business plans combing through detailed financials and metrics, to those who were never exposed to a startup pitch before judging that competition.

3. Judging Skews in Weird and Unexpected Ways

I had one flawed assumption in my thinking about the potential success of my pitch - I assumed that the judges considered the pitch the sole basis of selecting the winners.

However, the truth is, most judges inevitably take WAY more into account than just the pitch. Inevitably, in deliberation, weird variables like "what impact does this create" or "how far along is this company" get factored into the decision even though it had nothing to do with the pitch, see below.

From the College Dorm Room to the Venture Stage

I had an experience where all of this hit home.

I was judging a pitch competition for college students. One of the companies, Afforai, a startup that distills complex research into simple, digestible pieces using AI, was quite more mature than the rest of the students pitching. Co-founders Alec Nguyen and Austin Nguyen from Lawrence University had a solution built and was holding back the dam of customer demand for their product. Alec and Austin had a polished pitch with great sequencing and transitions to each co-founder that was speaking. Going into the judges deliberation, Afforai was my favorite and #1 pick.

In the judges deliberation, Afforai was an early exit from from the 1st-3rd place discussion. I was confused. I made the point that they had the most traction out of all of the companies and was the furthest along, quite a feat for being full time university students. Yet, some other judges didn’t evaluate it the same way I did. They saw the top three of the winners through other lenses such as, “who needs the prize package the most in order to develop their product,” “a good cause,” and “that founding team was incredible.” So, the cadre of judges settled on a top 3 with Afforai not taking home any prize.

After the first-third place winners were announced, I shot a look over at the Afforai team. They were visibly dejected. I think they had assumed, as I did in Chicago in 2018, they had the competition in the bag. Alec, Austin, and the rest of the team came up to me nearly immediately, still visibly bothered, yet humbly asking me how they could improve in their pitch.

I felt a bit awkward as I didn’t have much of an answer to give them. I knew how drastically the judging skewed across many non-pitch or even non-business related items.

I fumbled for words, but recall saying something like, “Just keep doing what you’re doing.” 

After the pitch competition, Alec and Austin followed up with me, clearly leveraging the exposure that the competition had given them. I was happy to have a chat. It wasn’t the best fit for Tundra Angels at that time. Yet, it's been exciting to watch their journey since.

Unsurprisingly, just a few months later, Afforai took off.

That Summer, Afforai secured $100,000 from Sputnik VC in Austin.

Then, six months later, Afforai announced an investment from Plug and Play Tech Center.

Then, recently Alec was featured on AppSumo’s YouTube channel in this cool interview! 👇

Closing Thoughts

Set realistic expectations about pitch competitions - many variables are out of your control in selecting the winners - the judges, the deliberations, etc.

Pitch competitions are mainly about exposure. Make the most of the exposure by having a quality of pitch that eclipses all of the other pitches by a long shot. There is often one clearly superior pitch and a sea of sameness for the rest of them.

Above all, don’t be fooled. Pitch competition winners do not translate to the likelihood of achieving VC funding. It’s about the opportunities that the competition exposure brings, not the prizes that you haul in.

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