About six years ago I announced on this very blog that I was done with venture capital. Kaput. Over. I was going out on my own, bootstrapped, never to rely on another dollar of VC money.

Things can change.

Shovels announced a $5M Seed round earlier this month. I'm proud of it. I wanted it. I still want it, and I still don't regret it, and I don't think I ever will. We will need this money and we will turn this $5M into many multiples of market value. It's invigorating.

So, what happened between 2019 and 2025?

To put it succinctly, Shovels happened.

I'll start from the beginning.

Coming off of MightySignal, where I took over leadership, I was convinced that I wanted to start another data business. I decided three things would have to be true about this next data business:

• It needed to be related to the real, physical world.
• It needed to be helpful to climate companies.
• It needed to be a big idea. Like, really big.

I could determine the first two points on my own, but how would I know if the idea was big enough? There's an obvious answer: get validation from VCs. I'll know it's big enough if I can raise money for it!

For the pre-seed, which I raised when we had no revenue, I just got lucky. Zach Coelius from Coelius Capital knew me (or really, just knew of me, but that was good enough!) So, I was able to raise the $1M I set out to raise when I wrote my business evaluation of Shovels.

My takeaway from pre-seed, btw, is that it's a crapshoot. You're pitching the highest of high-risk investors. These guys are the definition of crazy. To find one to lead your round, you just have to get lucky. Here's what needs to be true, all at the same time:

• The investor likes you
• The investor already believes the business opportunity
• The investor is currently investing

For all three to be true, lightning has to strike. You get lightning to strike by continuing to pitch. You get intros, you prepare, you meet and pitch. You follow up.

When you get the right investor, it moves fast. Don't waste time with the slow ones. Don't waste time with the ones who don't already believe that your market is massive.

That's my pre-seed advice.

Now here's my seed advice. I call it "O to 1, 1 to 10".

The first phase, 0 to 1

Every entrepreneur starts with a 0 to 1 idea. There's no other choice. Your first idea is the most practical version. It has to make the most sense because you've rolled that thing around in your head like a rock tumbler and what comes out is smooth and... practical.

Practical is a good thing. It helps you focus on making money, inch by inch, step by step. You have to break it all down into small pieces or you'll choke.

Now here's the thing. Most 0 to 1 ideas can be bootstrapped. You probably don't need money to do it. Or maybe you need some, but you certainly don't need millions of dollars to build your practical idea.

If you did need all that money, it wouldn't be practical!

This is the irony of fundraising in this stage -- you know you're supposed to ask for money, but you know deep down that you don't really need it. Sure, you want to pay yourself and your co-founder, but what's that? $250 or $500K for one or two years? You can't pitch the big guys with that small of a raise.

So you struggle with the slides because there's a little voice asking you why you're asking for so much money. You find ways to convince yourself that you need it and hope to find an investor who believes you.

To be clear, this is all perfectly normal. I've been here many times. Shovels was here once too, but I got lucky and pitched a 0 to 1 idea to someone who saw the path from 1 to 10. I'll explain this part now.

The real phase, 1 to 10

The 1 to 10 is what happens if your practical idea is successful. The earlier you figure out what this is, the better.

It can take a while, though, so be patient and listen to your customers. At some point, the pattern will emerge and you'll realize your perfectly practical idea was really just one piece of a much larger puzzle.

You'll be amazed. The investors you pitch will be flabbergasted. Everybody will love it! This is when you can recruit top talent, raise a ton of money from the best investors, keep everyone around you motivated. This is the 1 to 10 phase.

I learned this the hard way.

When Shovels was doing well, growing at a healthy clip, I decided to raise what we now call a "seed" round. Our first was $1.5M, a healthy "pre-seed." I decided that with more than $350K of annual subscription revenue, I was ready to open up a round and let everyone give me money.

I struggled with the deck. It was very... practical. There was nothing wrong with it, but it didn't sizzle. I got plenty of meetings but I couldn't close anybody. Even my super excited lead pre-seed investor was out. He didn't think I had the vision yet.

I was confused and disheartened.

Then I went to New York City for Climate Week and had a bagel with one investor who focuses on story. That's his value-add -- messaging and story -- and he told me about a company that he loves that helps police departments identify patterns in retail theft. Since thieves (shoplifters, primarily) operate across police jurisdictions, it's not easy for them to catch the scent when there's a stealing ring. So he invested in a startup that solves this problem for police departments.

"Isn't that boring?" I asked. "And isn't that market size really small? How can they build a big business selling software to police?"

"Police departments is just the start," he said. "By figuring out how to solve this problem and get police on board, they had all the social proof and learnings they needed to sell direct to retailers."

Software for police departments to see misdemeanor patterns across jurisdictions is the 0 to 1.

Once there, they can expand to every retailer in the country. That's the 1 to 10.

I understood what he was telling me. My current vision for Shovels, to find more ways to sell permit data, was actually still the 0 to 1. There was another missing step, and it was holding my story back. I needed to find it before he or anyone else would invest.

That was September. By October I had the scent. My team flew in for our twice-yearly summit, and at our final session I shared with them my vision for the future of Shovels: local government data, all of it.

Permit data is the 0 to 1.

Everything else is the 1 to 10. By establishing ourselves as the leading provider building permit data, we unlock the opportunity to sell everything else. And by getting everything else, we create a data network, which also becomes a valuable moat.

I closed our $5M seed round the first time I pitched it. True fact.

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I believe that at least right now, today, this is the way to fundraise. It could change tomorrow, but right now, even if you're raising a pre-seed, include something, anything, even just a guess about what your 1 to 10 will be.

I guarantee that it will help you close!