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“The fox knows many things, but the hedgehog knows one big thing.”–a Greek quote made famous by Isaiah Berlin

I first met Andrus while the two of us were pitching at the Estonian shark tank in 2012. A year later, we got to work on a marketing-related slide deck for Pipedrive. We’re different animals. To keep it simple, he’s a hedgehog — driven by one big question: “What’s the smallest thing you could build?”. I, in turn, am a fox puzzled by the science of complexity.

Because of this difference and the fact that the man has some sick skills…


Pitch Confidential #001: Yrjö Ojasaar of Change Ventures

Pitch Confidential is a series of candid conversations on fundraising, sales, leadership, and communication. The show combines street-level insights from practitioners and a quant-like focus on data. Each episode aims to reveal the ‘kitchen-side’ stories from pros who do the legwork.

To deliver on that promise, the first one kicks off with self-deprecating banter. It then continues with a run-through of the fund’s fact sheet. This written piece builds on the content of the episode. It also adds a layer of analysis and insight to help founders prepare their stories for the…


Virtual Demo Day Edition

Startup Wise Guys Demo Day at TechChill 2020

Picture a parade of a dozen or two founders delivering 2 to 3-minute pitches in front of a packed room of investment firms. The partners at those firms are sitting on folding chairs while rocking their fleece vests or branded T-shirts. They are in charge of deploying capital they raised from their limited partners, and EIF.

Their pitch comes in the form of an investment thesis, which should, in theory, lead them to invest in top global founders. Around 3/4 of them will fail to deliver the promised returns to their limited partners. …


7 data-driven tips for having conversations with investors.

Feels a bit empty.

During the past weeks, I’ve done webinars with over 150 founders ranging from Oman to Poland. Just over a month ago I’d be preparing them for high-stakes presentations in front of packed conference halls. Today, the limelight got replaced by desk lamps. The coveted headset stage mics and pics gave way to pixelated video feeds and your laptop’s standard stereo set-up. The same set-up that lets everyone know when your cat is hungry unless muted.

Meetings, networking events, conferences and conversations moved to Zoom, Crowdcast, Hopin, Slido, and Slack. Some of the tools aren’t new and have been around for…


How to speak to your audience’s sense of logic

Auguste Rodin’s “The Thinker” on display at the Peabody Essex Museum’s exhibit: “Rodin: Transforming Sculpture.” (Andrea Shea/WBUR)

Before becoming a go-to stock image for philosophic quotes, Rodin’s “The Thinker” was originally part of another merrily named sculpture — “The Gates of Hell”. Those very same gates that Dante and Virgil pass through to take the scenic route through the nine concentric circles of Alighieri’s Divine Comedy.

Once they ‘leave all hope’ and pass through, they enter the vestibule, a place for the ‘uncommitted’—individuals who did not use their intellect to make a choice between ‘good’ and ‘evil’, and as a result were denied entry to Heaven and Hell. …


5 pitching habits to fight the forgetting curve

Slush 2016 Founders’ Stage — Mark Lee, Head of Growth at SendBird pitching in the Slush 100 Finals. Photo by Jussi Hellsten. Slush Media.

Here’s the fleece-vest-wearing elephant in the room that founders tend to ignore: the average European conference can have anywhere from 100 to 300 investors in attendance. Major ones like Slush and Web Summit have upwards of 1,100–1,500, with significantly more attending startups than investors by a ratio of 2:1.

Around 100 to 200 of those startups deliver their pitch onstage. Each of the investors, ranging from a business angel to an associate or partner at a VC firm, in turn, might listen to around a 1,000 pitches a year from said pitching stages or in 1:1 meetings.

Yet, due to…


How to survive the first 3 minutes of your talk

Skype University Hackathon 2016, Pitch Training. Photo by Maido Parv

Former U.S. President Barack Obama (and probable greatest speaker of our time), listened to Eminem’s “Lose Yourself” to mentally prepare for his 2016 DNC speech, and the 24.4 million people who would watch it. At 00:53 Eminem spits a visceral set of rhymes on what it’s like to lose it on stage. To put it mildly, these two men could not be more different. One rapped his way up from a working-class Detroit neighborhood, the other an Ivy League lawyer who had to learn how to speak like a preacher rather than an academic. …


A 7-point guide to speaking with meaning at conferences

Conference artifacts.

Conferences are boring. Not the Elon Musk kind of boring. The kind that makes you, the attendee, want to saddle a Falcon 9 rocket home to binge on the latest seasons of American Gods, Billions, and Silicon Valley. All of them in one glorious, dopamine overdose-inducing sitting. That, or you could get your fix of the blue and white Facebook feed that shaves off fifty minutes of your life every day, and makes a fresh data pie out of it. The same Facebook that sells that data pie to advertisers to “bring the world closer together”.

Or, you could open…

Gleb Maltsev

Data-Driven Pitch Coach

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