Happy Thursday! As always, let’s dive straight in.

I often get asked about my best investments and my biggest mistakes.

The best investments? Easy - everyone loves talking about their wins.

The mistakes? Those sting more - but you can learn more from them.

Here’s one that still bugs me - not because the fund is doing great (I’ll also be covering great funds I’ve said no to and would still say no to), but because the things that made us uncomfortable were fixable. This wasn’t a fundamental miss on strategy or people - we just didn’t do the work to close the gap.

Back in 2018, I met Alpine Investors for the first time.

I really liked what I saw. The value creation model was different. The people-first methodology wasn't marketing speak - it showed up in how they talked about portfolio companies and talent development.

But there was so much noise in the track record. High unrealized marks everywhere. We just couldn't get comfortable with what was real versus what was fundraise aspirational.

We passed.

And at the time, it felt like the right call.

But here's what we failed to make clear in our own process: we didn't pass because Alpine wasn't "good enough." We passed because there were "hairs in the soup" - fixable concerns that just needed time to resolve.

We failed to do that.

Summer 2019. San Francisco. Second meeting with Alpine (Mark Strauch).

By this point, I'd moved to a new firm. And many of those unrealized marks from 2018 had now converted to actual exits. The track record was clearer. The story held up.

There was just one problem: they were done fundraising. We knew it going in. So did Alpine. This was a relationship meeting, not a pitch.

When we walked out, my colleague and I looked at each other and said: "We might have missed this one."

Except this time, we didn't make the same mistake twice.

Alpine fit our strike zone - mid-market buyout, $500m+. But our coverage wasn’t refreshed often enough. They moved into range, and we missed it. By the time we met them, it was 2018 and they were already in market.

Meeting a manager for the first time while they're actively raising is the worst time to meet them. Everything is polished. The story is rehearsed. And you're trying to make a high-conviction decision on a compressed timeline with no prior context.

If we'd met them a year earlier - tracked them through our normal process, heard a consistent story, watched the track record develop - we would have been much more comfortable when they showed up raising capital in 2018.

Using our A-E rating system, Alpine was a clear B after that first meeting. Good signs, but open questions on realization and proof. The problem? We treated them like a C after we passed - meaning we went quiet instead of staying close.

After we passed in 2018, we should have stayed close. Really close.

We should have been monitoring every exit. Every fund close. Every signal that could have made this a viable opportunity for us. Because here's the thing: it didn't lack a lot. We weren't miles away. We were uncomfortable with a few specific things that were entirely knowable and trackable.

Instead, we moved on to the next manager. And the opportunity closed.

After that San Francisco meeting, we immediately gave Alpine an A rating and tracked them properly. Every investor update. Every team update. Every signal that the 2019 realizations were becoming a pattern, not a one-off.

Through a lot of virtual meetings during Covid, it was undeniable. Alpine was executing exactly the way they'd said they would. The model was real. The track record was holding up.

When they came back to market in 2021, we moved fast. We invested in their next fund.

Below, I show in FundFrame Pulse how this should have been managed - the simple tracking workflow that would have turned a missed “no” into a well-timed “yes.”

You can click this link to see it: https://www.loom.com/share/9caaa89f60f64067a3af808eae1a7867