I’m just coming off of a conference in Madison where I participated in a founder/investor speed dating session. Seven minute in-person speed meetings, with founders rotating through tables.

In fact, I have a special connection to the room where these investor intros were held. See, for three years (2016-2018), I was on the founder side of table pitching my FinTech startup. For the last four years, I’ve been on the investor side of the table through Tundra Angels.

Reflecting on those last eight years, there are two realizations about in-person speed dating opportunities that I wish I would have known as a founder in 2016.

1. Understand the questions that investors are trying to answer in these contexts.

2. Know what founders should try to do

Understand the Questions that Investors are Trying to Answer

In an in-person speed dating scenario lasting a short, defined time frame, there are three main questions that I as an investor am seeking to get answered. The three main questions are:

For this startup,

• What is problem/solution?

• What is the traction?

• What is the urgency of this fundraise?

This may surprise you, but in the moment, the last question is actually the most important.

There is no way for investors to vet out the variability of the problem, solution, business model, traction, etc. in a quick 7 minute chat. Instead, investors grab onto a variable that they can control.

✅ Investors, especially in this situation, evaluate startups by how close the funding round is to filling up. ✅ 

The investor needs clarity as to if this is an opportunity that needs to be decided upon in the next few days… or weeks… or months. Depending on the time frame, the investor essentially rank orders their urgency to follow up in terms of this variable.

Whether founders like it or not, those startups whose rounds are closing in weeks get a priority decision over the ones who are 15% committed and likely 3-4 months away from closing. It doesn’t mean that each startup is unimportant. It’s just that because timing is the limiting factor of a fundraise, investor hierarchically rank their follow ups by the timeframe to close.

Know What Founders Should Try to Do

✅ The founders’ goal in the quick investor exchange is to be memorable and to create a hook of future intrigue. ✅

7 minute time slots go by very quickly. Especially back to back to back. The founders’ goal is that the investor should be able to reflect on their time and think of that founder and company saying, “That was an enjoyable conversation."

Three Tactics to be Memorable in a Quick Investor Conversation

1) Understand the context of the investor right up front

After sitting down at the table, founders can open the conversation with a simple, “Tell me about [investment firm] and the kinds of things that you invest in.”

The investors’ response to this question sets the stage for the level of detail that the founder should share in communicating the overall opportunity.

As a FinTech founder myself in professional bond trading, too many times I jumped right into my pitch and the investors' response after my monologue was, "I don't know anything about bond trading." Or, "We invest only in Series A." Translation: Me trying to get the train on the right track. Instead of pitching them, I could have gotten context and then have a way more productive conversation.

If the startup is in the FinTech space and the investor doesn’t invest in FinTech, that should signal to the founder that they likely need to add more industry context when sharing about the problem and solution. If the startup is in CPG, and the investor says that the firm is is focused on CPG and MarTech, then the context about the space the startup is in may largely be assumed.

To give founders a leg up, I often volunteered Tundra Angels' thesis information at the beginning because I knew that it would be helpful to the founder. But most founders came ready to pitch me, not to ask about what Tundra Angels invests in.

✅ It’s important that founders know the head space of the investor so that founders can tune their talk track to the investor in the moment. ✅

2) Come with the one-liner, problem, and solution explanation highly scripted

When I was that startup founder, sitting on the other side of the table just seven years ago, I wanted to come off friendly and warm. So, as to avoid being too rigid, I didn’t have much of a plan coming into the investor conversation.

Speaking now, as an investor, the best conversations are the ones that are the most understandable.

The best way to do this is to script your opening monologue. I would develop a very short scripted monologue around the one-liner of what you do, as well as in your explanation of the problem and the solution. After you finish the portion about your solution, then stop and say, “I’ll stop there and see if you have any questions.”

From that moment on, it’s not as necessary to have a script because you don’t know where the investor will take the conversation.

The scripted approach of communicating the one-liner, problem, and solution is highly intentional for two reasons:

1. It allows the founder to focus on the investor across the table without hesitating on what you are going to say. This scripted approach demonstrates that you are polished and prepared. In in-person settings, this impression is critical.

2. Additionally, the scripted approach also allows the founder to plant intentional words with an intentional purpose. For example, as developed in my investor meeting journey, I used a memorable zinger that I would re-purpose over and over again. It was, “It’s been said that the bond market is stuck in the 19th Century.” This was an actual quote that I found from market research, and I loved it.

This reference to the 19th Century was memorable, especially in a conversation about the technology of the future. The quote stuck out and created a hook.

Script the one-liner, as well as your explanation of the problem and solution. Then, say, “I’ll stop there and see if you have any questions.”

The investor will have questions. Trust me. It wouldn’t be venture capital if we didn’t get a word in. 😀

3) Have a one-pager that you reference while talking

From the four years of investor speed dating that I’ve done, the vast majority of founders didn’t come with any visuals and intended to have a casual conversation.

If the founder(s) did have visuals, they were intended to be leave-behinds and the founder didn't reference them during our quick chat.

That’s how founders can be different.

See, my most memorable speed dating meeting happened several years ago. I still remember when one founder pulled out a one-pager that the founder pushed in front of me. The one-pager had a collection of visuals, with six PowerPoint slides on a page. The one-pager was double sided. While the founder was speaking, using a pen, he pointed to each visual.

I could see the paper. I could feel the paper. All of a sudden, the founder's words started to glue to my mind. At the end, the founder left the one-pager with me.

I don’t think this founder realized how this approach hacked my mind.

✅ Even writing this now, I still remember that founder, the name of the company, what the founder was wearing when we talked, and what the one-pager looked like. ✅

It’s crazy how a simple one-pager with PowerPoint visuals created a step-function change in being understood and being memorable.

I also appreciated this no-frills approach with the one-pager with slides. I've been pitched before with slides that the founder shows on a laptop. Yet, a laptop has never had the same effect as a simple one-pager with visuals. The one-pager activated my senses in a way that casual conversation or even a laptop with slides could not.

Closing Thoughts

In quick investor speed dates, investors seek to answer three questions:

• What is problem/solution?

• What is the traction?

• What is the urgency of this fundraise?

Investors, especially in this situation, evaluate startups by how close the funding round is to filling up. 

Realize that investors see their next steps through this lens.

On the founder’s side, the founders’ goal in the quick investor exchange is to be memorable and to create a hook of future intrigue.

Three tactics to do this are:

1) Understand the context of the investor right up front by asking about their investment thesis

2) Come with the one-liner, problem, and solution explanation scripted, then open it up for questions

3) Have a one-pager that you reference while talking

Investors, especially in highly short and frequent investor meetings, encounter what I call the Sea of Sameness. Everything sounds, looks, and feels the same with little differentiation.

That’s exactly the arbitrage opportunity for founders.

With these three tactics, the founders optimize for the most important metric while speaking to investors - the ROI of being memorable, and being understood.

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