A Million Dollar Pitch: Part 2.

Sergey Leshchenko
4 min readOct 15, 2023


This week was nostalgic: I got to engage with a bunch of Ukrainian start-ups and gave a few consultations based on my experience of raising funds back in 2017.

As we established in the first part of the story — naiveness, creativity and the number of tries can do wonders. At the same time, the end goal of the pitch is never closing the deal — it’s only a tool, according to Sam Eisember — to get people's attention for further talk.

After we had gained the attention of our future investor in July 2017, he asked us to meet with Vladislav — the fund’s financial analyst. I remember how heavily we relied on the word “financial”, and would bet hard on our Fin. Record document with all the data as it pertains to our sales and everything. Vladislav was a charming and kind individual, who we hit off with right away. You see, you never know what’s the person's real task at hand when he’s traveling the city to meet with you. I believe — and Vlad can testify to this — that part of his job was to see if we were stand-up fellows who could present ourselves well and share the good vibe. We presented the business, exchanged a few thoughts, but most importantly — exchanged a few laughs. The Fin Record document was secondary.

The lesson here: Don’t Rely on Documents more than on your Personality. Figures will change, but your personality — never.

Now, let’s get to the most interesting part: our first meeting with investors in their favorite restaurant. If you want to read the article I wrote in the aftermath of the meeting — here it is. My views of this world have changed dramatically since that time, however, these are the lessons that persist:
Be Yourself. When you are talking to the investors make sure you show the traits that make you — you. I, for example, wanted to make them laugh and invariably cracked a few jokes. One or two landed. But that was enough.
Don’t be afraid to Look like a Fool. If you can’t admit that you are a fool in certain areas talking to your future mentors — you’re losing the chance to ascertain that they can become the ones. It’s vital for men in this world — we want to become mentors, therefore, don’t rob your investors of the possibility to become ones for you.
Always speak to the matter of how the money will be earned, not spent. It’s always a great starting point but for some reason, folks talk a lot about spending money rather than earning it.

To wrap things up, I would also like to point out some remarks as they pertain to presenting business ideas in front of an audience:

  1. Make Sure you are Bursting with Healthy Energy. Out of 7 pitches I witnessed yesterday, only 1 was filled with healthy energy. And the word “healthy” is instrumental here. You see: people are extremely socially attuned animals, we can sense bullshit and arrogance. One kid was also filled with energy, but you felt something was off — that was precisely entitlement and complacency in his speech. People don’t like when someone is overly confident. Confidence goes in healthy amounts — understanding that you know your stuff but at the same time being open for feedback.
  2. Don’t Make a Shit Ton of Slides with Small Fonts. Your slides should elicit emotion. It shouldn't take attention from the presenter. When the audience is trying to read what’s written on the slide they forget where the spotlight must go. And that’s always the presenter.
  3. Be honest. I enjoyed listening to the presenter of https://yourochi.com.ua — for the sole reason that he wasn’t boasting with some made-up accomplishment but was blunt and to the point. Even though guys don’t have sizeable sales, the sales index grows from month to month, and that’s what holds the most value.
  4. Smile, accept praise, don’t confront criticism, and humble yourself. If you need to counter the objection — do that, but be respectful and don’t create an image of a total jerk, who doesn’t care for anything that’s being said.
  5. Learn the language. The better you know the language — the easier it will be for you to maneuver around. It's cool to see folks not worrying about the English level in some cases, but honestly, even if you need to use English once a month for your board meeting — I’d rather make sure it’s mistakes-free.

With that, I’ll sign off and wish you a productive week ahead. As always, you can reach out to me for advice or consultation — always happy to help.



Sergey Leshchenko

I’m a Proud Ukrainian. I write in 2 languages. Mostly about business and personal development. I have co-founded DexDigital. Now I develop Beverly Production.