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The Leader's Mindset: Deep in the Trough (And Still Building)

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Every startup has a honeymoon phase, but eventually reality hits: the infamous “trough of sorrow.” In this video, Kenny talks openly about being in that stage right now—fewer clients than hoped, tougher investor conversations, and the financial strain that comes with it. It’s raw, it’s real, and it’s part of building something that matters.

But the trough isn’t the end of the story—it’s the proving ground. Having faced hard things before, Kenny shares why he sees this as evidence that greatness is on the other side. Every pivot, every fundraising lesson, every late-night problem-solving session is making both the product and the team stronger. It’s about building while in the valley, knowing the climb out is what makes the journey worth it.

Tags

startup pivotsleadership mindsetstartup journeytrough of sorrowfundraising lessonspersonal resilienceentrepreneurship challengesbuild through adversitylaw firm tech startup

Transcript

What are you thinking about? What are the challenges you need to overcome? And how are you thinking about doing that? So the startup stuff that I did in the early days, you know, it kinda lays out the startup journey. And startups usually start off all exciting and fun, and then eventually there you go through the trough of sorrow. And then if you can survive the trough of sorrow, then hopefully you find success on the other side. We're deep in the trough of sorrow right now. And the trough of sorrow looks like not enough clients, which means not enough interested investors, which means not enough money to pay the employees, which means all the problems that come with all of that. But I've been through hard things a few times now. And, if anything, going through this hard thing is just evidence that once we get through it, because we're gonna get through it, that we're gonna have something great. We're gonna be dope on the other side of this. We're gonna have learned a bunch. I've learned already learned a bunch through this process. So much about investing or I mean, getting investors, fundraising. That's the word. Yeah. And, it's gonna make us better. It's gonna make our product better at the end of the day. We're we're pivoting. We're changing. We're growing. We're making up we're making moves in real time.