As a founder, I used to wonder what an investor thinks about when they decide which startups to meet with prior to a conference or an event, etc.

This past week, gener8tor, one of our great co-investor relationships, offered to me an opportunity to meet with many startups.

In today’s article, I decided to illuminate here what I wish I would have known.

Gener8tor presented me with a list of companies in Airtable this past week. The list looked like this and had hundreds of startups on it and several many more data points across the companies, such as business model, product keywords, etc. They asked me to submit my meeting request by a certain date.

I want to articulate a mental framing that is threaded between every time I go through a process like this and select startups to meet with.

You may have heard it said that investors invest in lines, not dots. In my head, I think of it more like a snapshot in time vs. a panorama.

A snapshot shows a still picture where the company. 

Many snapshots over time allow you to put together a panorama of that company and see the progression over time. 

The progression over time is of utmost importance when it comes to venture capital investing.

✅ It is only with time that one discerns the closest approximation of the true reality. ✅ 

One or two snapshots in time are interesting, but only after more snapshots in time come into focus that a panorama can be put together. Only after a pattern, a panorama, is put together can one see how the founders execute, or the market reacts to the product, or how the GTM strategy is working, and a myriad of other variables. 

That's the mental framing that I bring to viewing a list of startups to meet with. With that, let's step into my investor head this past week and review the list together.

My first pass is I immediately start filtering the list based on things that fit our strike zone of thesis. In the case of Tundra Angels, we have a geographic focus and at this time only invest in startups in the state of Wisconsin. Other investors would sort based on variables relevant to them - geography, stage (pre-seed, seed, Series A, Series B), or by industry, or venture capital raised, revenue, etc. 

So in my case, I filtered with the company “state.” 

Regardless of the context though, shrinking the world to a more readily reviewable consideration sets up the investor’s next set of analysis. 

Next, I go down the list of company names and note which companies I recognize, and which ones I do not recognize. Which ones are new to the list and which are ones that I’ve seen before?

For the companies we've seen before or met with, this is where some of the other data points come in. As mentioned above, I am focused on snapshots over time that point to the company’s panorama. 

I ask the question - has there been a meaningful change in the traction? I compare their current traction (revenue, funding, product status) to that of our last interaction. 

I saw Company X, which listed a few hundred thousand in annual revenue and several hundred thousand raised. I like the founders, but based on what I recall from the traction last time the last time I saw the list - this was not a material change. 

I clicked through a few pitch decks, mostly to see how things may have changed since last time beyond the numbers on the sheet. 

It turned out that several of the companies were in the same bucket as Company X. Similar revenue numbers in capital raised, or lack of capital raised, than last time I saw the list. They had a very similar traction story to the last snapshot. 

Now to take you into my mind, when I'm reviewing this list, I'm thinking about every single startup in context and thinking about the market and their product. 

Again, this is all about discerning the closest approximation to true reality. If a lot of these numbers do not change, then it gives me, as an investor several signals - it could be that the company is still bumping along on the same trajectory. It could be a bit of a statement on the founder or co-founders execution. Or it could be totally independent of the founding team, like the market. 

In the case of one particular company, I observed a very little change in their traction. I recalled the conversation that I had with the founder a while back where we discussed the market itself being challenging and the product being slower to adopt because of the incentives that existed in the market. 

So when I see data points like that, objectively, I either put it in the category of “They're still having the same struggles that we talked about at the last chat.” 

In instances where there is not a material shifting of traction, investors like myself prefer to reserve their time for companies where there is a material shift in traction. 

There were two companies that I had met with previously that seemed to have material changes in their traction.

Company A was one that I had met with before. The revenue number was quite a bit higher than the last touch point with the company. 

I considered another touch point. Over the months, the CEO had been doing a nice job of keeping me and other investors in the loop with the progress via email. That shows well to me. A good quality. 

Lastly, through one update from the CEO, I was aware that this company also recently went through a startup accelerator. Yet, I had not talked to the company since then. 

Between the revenue being higher, the accelerator program, there seemed to be a different level of tempo. So I selected them for a meeting.

There was a second company that caught my eye. I too had met with this one at one point. The company listed revenue in the tens of thousands of dollars. Last time I interacted with them, I don’t think they had any revenue. 

The company also listed several hundred thousand dollars of funding raised. That surprised me. I wasn't aware that they had raised a round, not to mention several hundred thousand. Last time I talked to them, I don't think they had raised anything. 

Furthermore, independent of the data points on the sheet, I recalled an email conversation some time ago that I had with a seed Stage VC where we were exchanging deal flow opportunities. In our exchange, they brought this company up as one to take a look at. They didn't specifically list why, but I thought it was a notable callout considering the last time I spoke with the company. Collectively, this gave me a signal that the startup had a higher tempo than last time. 

So, I decided to request a meeting with this startup too. 

Then I go through the companies that I'm unfamiliar with. For these, I do quick hits on a couple of different aspects. There's lots of variability here, and every investor evaluates this differently. 

I check out the company description. I check out the revenue to date, if any. I check out how much funding they raise to date, and how much they are raising. 

In the case of Company Z, they had zero revenue and were looking to raise $100,000. Definitely early stage. 

So then I tried to ascertain the state of the product. The company description read like they were raising funds to build out the product. 

Then I asked myself about the company itself. Namely, is the company doing something where their technology is groundbreaking, or does it exist in a market with a business model where they could fly off the blocks to acquire customers rapidly? 

In the case of this particular company, the company description read like it was a me-too type product in an existing category. There didn't seem to be anything novel about what the product could do or would do that would make this major unlock for the market.

So in this case, given that they had zero revenue and seemed to be mid-stream in product, I decided to not pursue a meeting. The company was clearly raising funds to build out the rest of their product. 

If they had revenue in the tens of thousands, that would indicate a level of maturity with a product and company, would have likely been enough for me to request a meeting with them.

Now, the decision not to pursue a meeting for a company at this stage is definitely investor and market-dependent. For Tundra Angels, we find it hard to invest capital to get the product in the market unless we are highly convinced that this will take off. But in the case of this startup, this particular market was big but it was very noisy. A lot of players existed doing something similar.  

In thinking about meetings like this, investors are always asking for the ROI of their time. Will this conversation change my next steps in a meaningful way? 

Now, one may consider it rude or selfish to not take meetings with startups we've already talked to. 

But a lot of times, I use these opportunities for new top-of-funnel deal flow. Investor deal flow is one of those things that one always has to be uncovering new ground. Additionally, when I attend conferences over the years and there is an opportunity to select startups to meet with, I tend to always select companies that 1) I am unfamiliar with, and 2) for the startups that I am familiar with, have had meaningful changes in traction. 

The time allocation tends to go to the ones that are net new, or that show meaningful changes in traction.

I want to call out how non-scientific this process was. There was some analysis that went beyond what I just wrote, but at a high level, that was it. Because of this…

✅ I’m always suspicious of what I might be missing on lists like this. ✅

I'm always asking myself, "What is the story beyond the story that is reflected here?” Here is why:

✅ Startups do not fit tightly into black and white boxes. ✅

Breaking a startup into black-and-white objective filters to create a clean list of data for investors like me to consume is one of the hardest things to do in startups and venture capital. 

We assign names to categories - FinTech, Digital Health, CPG, etc., but nobody really knows what the categories do or not mean. What I consider a FinTech play may not be a FinTech play to another investor who looks at the same company.  

With filtering on the first pass too much, one might actually miss opportunities. 

For example, in the case of company geography, what should the founder put down in the case of a distributed team? What is the company “state”? Should it be where the CEO is located? Should it be where they are incorporated? Should it be where the majority of the team and its main office is? Every founder can rationalize the answer differently. 

For example, one of our portfolio companies, Gripp, is a spinout of Purdue University in Indiana. CEO Tracey Weidmeyer is based in Wisconsin, and his co-founder and CTO, Jenkin Lee, is based in Seattle. I’ve seen Gripp as a company listed as based in Indiana online. 

Is Gripp an Indiana company? Yes. Is Gripp a Wisconsin company? Yeah. Is Gripp a Washington state company? Why not? 

But if Gripp happened to be on the list and I filtered to the state of Wisconsin, there's a 66% chance that it wouldn’t have come up. 

Or, with industry. With one of our portfolio companies, Cylerity, it is an embedded financial tech play that uses AI to predict the pay-ability of healthcare claims and advances cash to the provider within 12 hours. So should the company be considered FinTech or Digital Health? For a black and white question on an application like this, what the CEO, Ryan Wheeler, selects runs a risk of alienating people who do not invest in either category. 

Thus, investors need to find ways to break past the black and white boxes to get more context beyond the sheet.

But overall, I have found that if an investor likes something enough, there is always a way to rationalize the investment. But at the same time, if an investor doesn't like something, the same language that they rationalize an investment with could be the same language to rationalize a pass decision.

I heard a story once from Mike Maples Jr. from Floodgate VC on his Starting Greatness podcast. On one of the episodes, Mike shares a story to the person that he is interviewing. In the late 2000s, one of his investor friends from Canada reached out to him. The investor said, “Mike, I know that you and Floodgate do Seed stage deals. I have a startup that is raising their Series A. I know it’s a bit later than you typically invest but I wanted to at least mention it. The startup’s name is Shopify.” 

But Mike Maples Jr. passed on the intro to Shopify. 

On the interview, Mike started bemoaning to his interviewee, “I should have had the presence of mind to take that pitch. But I passed because it was a later stage than we typically do.”

Startups do not fit tightly into black and white boxes. Even the best venture capitalists in the world can fall prey to that dynamic.

Yet in addition to presenting a risk of missing an opportunity, it also can present opportunities.

I got connected to one of our future portfolio companies, EVEN, on a deal flow list like this. I saw that CEO and Founder, Mag Rodriguez was on the list, saw his contact info, and sent him a note below:

I got on the Zoom call with Mag. In the first few minutes, we talked about the initial connection via the deal flow list. 

He says something really interesting. He said, “I'm going to be honest with you, I don't know how I ended up on that list.” 

He went on to share that they were raising funds but not actively soliciting outside investors. 

But when I reached out, Mag told me on that same call that he had chatted with Raquel Filmanowicz at VC 414 and Troy Vosseller from gener8tor, who both told him, "Tundra Angels and Matthew is legit. You should have a conversation with him."

Even though investors run the risk of missing the good, there's also good to be uncovered, whether or not the founder knows it or not. 

So what are startup founders to do about the non-scientific way that investors select to meet with them? 

Stand out from the sea of sameness. 

Much like when a startup delivers a pitch, it is way more about being different and novel than it is about being better. Find arbitrage. 

Find ways to clearly articulate what you do in one to two sentences. If there was a company description that had a single sentence for what they did, that would be different. 

There is no reason that you need to take up the entire paragraph or paragraph and a half of your company description. Use fresh language. Stay away from buzzwords. 

Don't spend time on things that really do not matter, such as perfecting the pitch deck design. An investor will scan it, if they scan it at all, for probably 10 or 15 seconds. 

Outside of all of this, there is also the consideration of optics. Being transparent, if you are always on the list and your traction story never changes, then investors tend to put you in a category that nothing ever changes for your company. It's very hard to get out of that mental category once the investor puts them in it. Thus, take the advice from one of my other articles, where I say Fundraise like a Brazilian Steakhouse.

But by and large, there is an aspect where, “You're raising, and I haven't heard from you?” It makes me wonder, what kind of investor outreach are you doing then? 

Startups have to put themselves in as many positions as possible to be seen and get attention. 

✅ You can't control which investor is looking and how they are reviewing.

Yet, you can largely control where you are being seen and how you are being perceived. ✅

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