Anna Deynego, founder of the Burning Heroes Founders Association — a nonprofit dedicated to creating equal opportunities for founders — shares her insider advice on winning startup contests.
As the founder behind a global movement organizing startup contests, I’ve seen thousands of pitch decks and listened to hundreds of pitches. It’s time to highlight what actually works. Startup contests offer a unique stage to reach investors and advisors without chasing them down one by one.
Here’s the mistake I see: founders treat contests like a game of chance. “With low odds of winning,” they say, “why invest the effort?” Here’s why: your effort multiplies by the number of investors and experts watching. With intention and preparation, it can be a game-changer. Here’s how to maximize your chances of winning — or perhaps make winning beside the point.
1. Think Like an Algorithm
“Algorithms don’t get charmed — they just tick boxes!”
Every contest begins with the application. Most initial screenings aren’t done by investors; they’re handled by algorithms or teams tasked with sorting thousands of applications. They need clear, checkbox-type information to make quick assessments. Helping screeners locate key information easily increases your chances of staying in the running.
Many applicants come at the idea stage, so if you already have funding, a product, or revenue, make that obvious.
If a pitch deck is required, ensure it addresses typical questions clearly: What’s the market? What’s the problem? Why your team? Traction? How are you (or will you) earn? Unit economics? Business model? Labeling your slides as “Market,’ “Traction,” or “Team” helps screeners find what they’re looking for efficiently.
2. Plant the Seed
“Make judges wonder, ‘Where have I seen this startup before?.”
Do a little homework on judges’ backgrounds, focusing on their interests, investments, or recent projects. No need to tailor your entire pitch, but highlighting aspects that resonate with their interests can create a favorable impression.
A few subtle “honey drops” — mutual connections or even light targeted ads — can spark a sense of familiarity. After the contest, a follow-up message reinforces that impression, providing an ideal reason to reach out and keep the conversation going.
3. Differentiate Like Never Before
“Boring doesn’t leave a mark. So, what’s your unique edge? Show it off or fade in the startup shuffle.”
It’s tempting to go with safe answers, but standing out is essential. Think about that one thing that sets you apart: a unique journey, an unexpected pivot, or a bold mission statement. Whatever it is, make it memorable early on. After hours of pitches, judges should remember at least one detail about you, Give them that defining spark.
4. Master Timing: Short, Sharp, and Seamless
“There’s a rhythm to every pitch – and nothing kills it faster than going over time.”
Contests follow strict schedules, and if you’re even a minute over, it disrupts the whole flow. Many promising startups lose their chance by being cut off mid-pitch. Be sure to finish your presentation on a strong note, not a rushed one. Have a timing structure for each key point and keep it engaging.
For online presentations, test your connection and sound quality beforehand, and don’t let tech issues eat into your presentation. Treat it like a concert — leave the judges wanting more.
5. Embrace Hard Questions
“Want to impress the panel? Ask yourself the toughest question in the room.”
Every startup has flaws, and that’s okay — judges know it, too. Instead of glossing over challenges, get ahead by bringing them up and addressing them head-on. This approach shows that you’re not only realistic but confident. You can say something like, “Our biggest hurdle is X, and here’s how we’re tackling it.”
Here’s a trick: prepare a “gotcha” question — the one you’d least like to answer. If no one asks it during Q&A, bring it up yourself. You might say, “If I were sitting where you are, I’d probably ask about… Here’s what we do about that.” This bold move earns credibility and impresses the panel with your honesty and insight.
Bonus tip: You Don’t Have to Win to ‘Win’
“Sometimes it’s better to be the underdog everyone remembers than the winner everyone forgets.”
Here’s a the truth: you don’t need to come in first to “win” at a startup contest. Being the underdog can work to your advantage. You gain exposure, you’ve made a great impression, and investors look for potential beyond the trophies. The true reword may be a handshake or a coffee invite from someone who sees your potential. In the end, that connection can be worth more than any award.
Startup contests are more than a chance to win — they’re a platform for visibility, connections, and credibility. When approached strategically, the benefits can go far beyond the trophy.
