June 5, 2023

Building a company with longevity can often be compared to getting a massive freight train to move. You’re adding cars to the train by building all the components of the product and you’re priming the engine by putting in place all the operational structures it takes to scale. Every little win, every small success, and the gears start to turn but it’s still slow going early on. The train crawls forward inch by inch and all the effort being put into it doesn’t seem to compare to the results.

May 30, 2023

In a year like this where markets are volatile and being able to predict how things are going to play out is harder than ever, it's inevitable that it won't always be smooth sailing. We managed to clear our lofty revenue targets in January, February, March, and April by grinding on all fronts and also catching a few lucky breaks along the way (as we always seem to be able to do). 

May 22, 2023

It's been a long road to get here and I recognize that the path itself has been difficult. We were forced to make hard decisions, rein in our spending, and oftentimes that has led to us having to change our culture to adapt to the new normal. While we've been able to hit the ground running this year with an incredibly strong start, we've also ended up losing some of what makes our team tick.

May 15, 2023

Today marks an important milestone in our company’s life. Five years ago to the day, we officially incorporated ourselves in our small office in Tribeca that we shared with a few other companies. Five years later and I could have never imagined we’d be what we are today.

The traditional startup playbook—raise big, spend fast, swing for the fences—is fading. In this episode, I unpack why the VC model is under pressure, how AI is fueling a new era of smaller, faster, more profitable startups, and why debt might beat equity for founders who want to scale on their own terms. If you’re still raising like it’s 2013, this one’s for you.

May 8, 2023

As we've been wrapping up the last remaining items for the Series B, we've seen palpable demand from so many investors who were forced to be left out. In market conditions that are more favorable, it's normal to just leave the demand as is and prime them for the next round of financing. In times like this though, it's never a bad idea to pad the war chest and prepare for the what ifs that could happen in the coming quarters ahead.

April 24, 2023

And that's that. We're done. We've successfully closed on our Series B. There's of course still a few administrative items to get to the finish line but all the commitments are in and ready to be signed for and wired. Amazingly enough, we were actually oversubscribed, with several groups this past week trying to figure out how to squeeze into the round with checks as large as up to $[ ]M beyond this $[ ]M we already have committed.

When you’re building a company from the ground up, you will make many mistakes. Learning from them and building core mantras from the lessons you glean will define how you think and operate during your journey. Mantras are born out of your experiences when scaling your company and from surrounding yourself with people who have been down this path before, imparting wisdom from their experience onto you.

This week, I sat down with Sean Smith, co-founder of SMB Investor Network, to talk about a very different slice of the private markets—entrepreneurship through acquisition. We cover everything from his leveraged finance days at CIBC to why he's now focused on buying HVAC companies and plumbing businesses. Plus, we discuss how private credit and SMB equity are surprisingly complementary when it comes to building a resilient, income-generating portfolio.

April 3, 2023

With that, we've officially closed the books on Q1. For the first time ever in the company's history, we've managed to post three consecutive beats on revenue and also the highest quarter ever for technology revenues. This is no small feat, especially in as volatile and unpredictable a year as this.