It is possible to hack the mind of the investor.

I didn’t know this was possible as a founder, until I had the investor who had just invested in my startup confess to me that that is what happened.

I’ve lived this. as a founder and now experience as an investor. There is ONE FACTOR that separates founders who successfully raise capital from those who don't:

The #1 factor is if the founder creates a spark in the first meeting or first interaction with the investor. 

It is not necessarily the startup itself, but how the startup is pitched, that makes all the difference. Let me explain. 

When I was a founder and CEO, our startup had built an algorithmic bond trading tool. At one point, I attended a large fixed income conference in Boston. At the event, I approached the Head of Fixed Income at Merrill Lynch. I met him, and had about a 30 second interaction pitching our bond trading tool. He listened.

When I asked for his business card to follow up, he reached into the pocket of his blazer, and seemed to pretend that he forgot that he didn’t have a business card on him - he intentionally forgot business cards. Then he said, “Oh, I don’t have one on me. Just look me up on Bloomberg.” 

With these words, he gave me a signal - “I’m not interested in this enough to hear from you again.”  

If he was interested to learn more, even if he didn’t have a business card, he would have given me his email address somehow. Even if it was a verbal, “I’ll give you my email. Could you write it down?” 

In my investor experience, here is the single most important thing for founders who fundraise successfully and those that do not: 

The #1 factor is if the founder creates a spark in the first meeting or first interaction with the investor. 

If a spark is created, investors give you continued access to them. The access could be a “Let’s have a second meeting,” or, “Here’s my business card,” etc.  It could vary, but a next step that signals, “Let’s continue to talk.” 

If a spark is not created, investors withdraw continued access to them. You likely get a pass email. They don’t schedule a second meeting. Or you get ghosted - they don’t see it as enough of a priority to respond to your emails. Access gets cut off, like it was for me at this Head of Fixed Income above. 

The spark is one part clarity, one part emotional connection, and one part kinetic energy. For the investor, it’s a feeling of, “I totally get this, resonate with this, now here is what I’m going to do next…” 

I want to propose a non-obvious way to think about your fundraise. The phrase a startup’s "fundraise" represents an extremely vague and a incredibly broad process that means a million things to different founders. 

✅ I want you to focus in on one specific moment in a fundraise - the first interaction / meeting with an investor. 

In my eyes, that “first” moment with an investor holds disproportionately more leverage than everything else that happens in a fundraise. ✅

To put it in a different metaphor, a first investor interaction is like an audition. If you are not memorable, if you don’t stick in their head compared to other founders at that snapshot in time, you won't get a “callback,” AKA a second meeting, a follow up, a “Can you please email me” request. 

Let me let you inside the Tundra Angels’ tent to show you what I mean. 

Tundra Angels recently committed to and is closing on a startup as we speak. One of the founders recently sent out a thank you email to all the investors in the round. In the email, the founder called out their lead investor, who I am excited to share at a later time... 

The founder said in the email, “To [Investor Name] ([VC Firm Name]), we knew you were the real deal from our first conversation.”

I want to repeat that - “We knew you were the real deal from our first conversation.” 

Something happened in that first conversation. A spark was created. And, the investor granted them continued access.

Now let me transport you to my first conversation with this same founder that led to our investment. 

When I met with this founder over Zoom, I felt that a spark was created. A three dimensional clarity, emotional connection, and kinetic energy powered me to take the next action. At the end of the first call, I booked a follow up call with the founder.

Coincidentally, I knew that this founder was the real deal from our first conversation. I’m sure the to-be-named lead investor would say the same thing about the founder. 

The first meeting or first interaction with an investor holds a disproportionate amount of leverage over the entire fundraise. 

✅ A successful startup fundraise, then, is an aggregation of first meetings or first interactions where sparks were created along the way.

An unsuccessful or challenging fundraise is an aggregation of first meetings and first interactions where sparks are not being created. ✅

There is a villain that lurks in every first meeting with an investor and prevents any spark from being created.

✅ It is the challenge of making the investor resonate with what you are doing within a very short window of 5-8 minutes. 

Put another way, the villain is the hyper short form factor of time that you have to give the investor clarity / resonance / and kinetic energy. ✅

I’d say this right here is the hardest part of fundraising. Hands down.

The founder has 30 minutes at the most on a first meeting, and needs to convey the story and the key points of the business in a 5-8 minute window on the front end of the call before the investor jumps in with questions. 

Most founders do not do this well. It’s not their fault though. It’s not their startups’ fault. 

It’s because they do not know how to make the investor resonate with what they are doing within a very short window of time, 5-8 minutes. 

The result? 98% of my meetings, and other investors’ meetings with founders have zero spark. No clarity, no emotional connection, no kinetic energy. 

Now, founders aren’t unaware. Most of the time, they know this is the case, but they don’t know how to get there.

✅ That's why the pitch and pitch deck are a continual source of founder insecurity. ✅

I can’t tell you how many times I get asked, “Can you give me feedback on my pitch deck?” Founders are always questioning, “What do I say, how do I position this, do I position this part of my business or that part? Do I talk about the future or the present? Are my slides compelling enough?” 

Founders seem to accept that there is no escape from the constant insecurity about their pitch and pitch decks. In turn, they accept the mediocrity of what it is. 

“This is just how fundraising goes, I guess.” 

But listen. It doesn’t have to be that way. I discovered a better way that I want to tell you about. 

I have found that the only way to create a spark is when the investor can’t get you out of their head. I discovered this completely by accident as a founder. 

When I was a founder, I created an investor pitch. Compared to other startup pitches that I heard, I thought my pitch was “fine.” It wasn’t bad… but also wasn’t amazing. I’d say it was “workable.” 

But over time, I started to get the feeling that something I was doing in my fundraise was off.

The enthusiasm level of the investors was always lukewarm. Never urgent follow ups, never scheduling a follow up meeting. Instead, polite and tempered language saying “We’ll get back to you,” which nearly always led to a pass decision or being ghosted.

I also observed that there seemed to be common patterns to my investor meetings - investors eyes would glaze over, clearly spacing out while I was speaking. They tended to ask questions that I thought I covered clearly in the pitch. 

“Something isn’t working here,” I concluded. 

✅ What I did next transformed my fundraise, and who I was as a CEO, and my entire life. ✅

I decided to change ONE THING. I re-worked my pitch in a way that I have never seen done before and developed a proprietary pitch framework in the process. 

I debuted it at a pitch to the Golden Angels in Milwaukee at the Northwestern Mutual tower downtown. (Shout out to Mary Hannes at the Golden Angels, now one of Tundra Angels’ great co-investor relationships!)

It was after that pitch that I heard something after that I hadn’t heard much before that:

“Great pitch.” “Wow, that was great.” 

The Managing Director of Northwestern Mutuals’ venture team came up to me and said, “That was a great pitch!” 

Then the investor follow up? Excited. Enthusiastic. Momentum. Energy.

In my pitch, I delivered a dramatic story and script about a person named Greg. The story had drama, memorable body language, and captivating visuals. But the way that I framed up the visuals, the solution, combined with a tight word for word script, it came off way more like a movie trailer than a pitch. 

I continued to use that same pitch everywhere I went.

In a pitch competition in Chicago in front of 500 founders and investors where every single one of the five judges complimented me on the compelling nature of my pitch. In a pitch competition in the Twin Cities to key FinTech strategics such as US Bank’s and Allianz’s venture team, etc. 

Everywhere I went - the outcome was the same - a long line of people, founders and investors, coming up to give me compliments afterwards. 

Instead of an Insecure CEO, I became a “Drop the Mic and Walk Offstage” CEO. 

I was becoming the CEO that I had always envisioned myself to be. Not because I took a leadership class or something - but because I carried a message that created a spark.

It was momentum rolling downhill for my fundraise.

Then, there was a moment where I realized why this all mattered for the fundraise. 

One of the startup accelerators I applied to is called the FIS Startup Accelerator, which invests in promising fintech startups that are relevant to banks and asset management firms. At one of the steps in the interview process, I met the Managing Director. Let’s call him, Shane. And I delivered my pitch to him. 

My startup ended up getting accepted to that program out of close to 300 startups that applied. On the first day of the cohort, when I met Shane, he said something poignant to me. Speaking about my pitch, he said, 

“I can't get the story of Greg out of my head.”  

My startup’s pitch was so good, that he was replaying it, over and over, in his head. I had hacked his mind.

When I heard him say that, I had this out of body realization. 

“That’s it. That’s what fundraising is all about.”

All this time, I was focusing on the wrong variables and making fundraising way harder than it actually could be.

In that moment, I realized - “It’s not about being the best startup out there. It’s about being the most unforgettable.”

✅ It’s about being the startup that the investor can’t get out of their head. ✅

Let me back up one month earlier to my third interview when we were still being considered for the accelerator program. Something happened during that third interview that I didn’t know how to place until Shane said this to me on Day One.

On the third round interview, I jumped on the Zoom call. On the other end of the call was Shane and several others in the room who I had not met up until that point. Shane asked me to go into my pitch - the same pitch that I gave through the first and second interviews when I met him for the first time. 

I gave my pitch, and delivered the conclusion. Then, there were a couple seconds of silence. 

Shane turns his head towards to the other people at the table that I didn’t know, and says, with the “Isn’t that good?”

The others chimed in, “Yeah, wow.” 

At that moment, I realized, “The Managing Director is literally showing us off right now. He wants others to have the same unforgettable experience.” 

My pitch had created a spark within Shane, and he wanted others to experience the spark too. 

It was that spark that led to us raising venture capital from a Fortune 500 corporation.

It’s not necessarily about being the best startup out there. It’s about being the most unforgettable.

Next week, I am opening up a course to help other founders create a pitch + script that creates a spark, just like this.

Up until this point, I have only coached companies that pitch to Tundra Angels on this proprietary storytelling and pitch framework. It works with raving results, as you can see by some of the founder feedback below:

If you resonate with this, drop me a note. The enrollment will only be open for a 5 day window. I’ll share more details when I open it up early next week.

Fundraising is a vague and amorphous process - but let me focus you in on ONE moment that matters - the first meeting or interaction with an investor.

If no spark is not created, you stand little chance of getting continued access to that investor.

If a spark is created, you will likely not only have access to them but likely also access to others in their network.

One of the amazing pieces to all of this.

When a founder creates a spark for investors, a fundraising round is actually closed by investor backchannel conversation. Investors talk to each other, pitch each other on the opportunity, to get them into the deal. It's investors who are empowered with a spark want other investors to experience that spark too, as Shane did in that room.

So, are you pitching investors? Or are you hacking the mind of an investor?

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