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If I wanted to say that there was a hard fundraise, it was not the seed round, it was not the Series A, it was the A extension.
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it was tough because it was a series of decisions that I had made poorly.
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We'd made progress, we'd focused our niche, we'd reduced our churn by a ton, we'd increased our speed at implementation, our customers were happier, the product was more fully built out, the team was stronger, but the market had changed.
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I had deployed capital and spent money as if the market wasn't going to change.
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I don't know how I would have gone back in time to change how I thought about that either.
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I think maybe people who watch this in the future, maybe they don't know how it felt in 2021.
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In the middle of 2021, it felt like growth was the only thing that mattered, and you were lame if you thought about efficiency or cost control, and oh my god, you could grow at 4x over a year and a half, why not do that?
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if you have that, grab the bull by the horns, grab the tiger by the tail, whatever it was.
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It was everyone, it was investors, it was employees, it was prospects, it was some customers were thinking about venture capital in manufacturing.
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It's that old tale of, right before big Wall Street crash, there were shoeshine boys that were talking about what stocks to trade.
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I should've, I layered those two concepts on each other and said, when, you know, small business manufacturers are thinking about venture capital, it might be a bubble.
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But, in the moment, I didn't.
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I had some sneaking suspicions, but I didn't have the courage to act on them.
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And I kept repeating to myself, what I've heard over and over again, you can't predict the future.
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You can only act on the information that you have.
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And the information that I had was, interest rates were low, valuations were high.
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I think the first sign was middle of 2022.
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This was about a year after we raised our Series A, we'd made some progress, we'd gone through some leadership changes, we'd fixed a bunch of problems, but it was really evident that things were slowing down.
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Interest rates were starting to go up, things were cooling down.
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The hype, noise, all the text messages and Discord messages and Slack messages I was getting about rounds getting fired off, and oh my god, it's so easy, and secondary, and blah blah blah, all this gamification of venture.
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That conversation started to die, and I think that was my first signal.
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Heading into 2023, I knew we needed to raise again.
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We were tapping into our venture deadline.
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We're cleaning things up.
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We did a very painful riff.
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We went from 70 some people down to just under 50.
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We reduced burn.
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But, you can't really, at that stage, cut your way into breakeven.
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At least we couldn't at the time.
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I knew we needed to fundraise.
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December of 2023, spent an entire two weeks thinking about what story we were going to tell, what was the accurate depiction of where we were, the lessons that we learned.
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In retrospect, we were probably a bit too honest.
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We really highlighted, we self flagellated a lot of the mistakes that we made.
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I don't think very many VCs actually even care that much about that.
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We should have highlighted some of the important things that we actually achieved and where we're going in the future.
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But we actually had some really great top tier investors want to invest in us.
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which was incredible, because very few term sheets were issued for anyone at the time.
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But, man, did it feel like SVB blew up in the middle of my fundraise, and I was eating three pints of ice cream a day, and I was working really hard, I was putting in 120 hours a week and feeling sorry for myself.
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Those emotions I felt in the seed round of gratitude and greed and all those things, I felt none of that.
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I felt exhausted.
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I felt depressed.
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I felt sorry for myself.
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I felt reluctant.
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It was an incredible round that we put together.
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It was something that was far more worthy of gratitude than our seed round, not to say that we shouldn't be grateful for the seed round, and yet I didn't feel any of those emotions.