Entrepreneurship is unpredictable—just when you think you’ve got it all mapped out, you're hit with a tough choice between two very different paths. One feels safe and familiar, while the other is full of potential, uncertainty, and risk. Every founder faces that pivotal moment: Do you play it safe, or take the leap? Today’s guest, Michael Diesu, co-founder and CEO of Revenue Roll, knows this dilemma all too well. From diving headfirst into the startup world against conventional advice to navigating a cooling fundraising market, he's made those tough calls more than once. Revenue Roll recently raised a $2.5M seed round led by Innovating Capital in late 2023—an impressive feat in one of the toughest fundraising climates in years. In this episode, we dive into Michael's journey, unpack his big wins, hard-learned lessons, and get an inside look at how he closed that seed round. But first, we rewind to the early days—because those initial decisions? They set the stage for everything that follows.

Fundraising can be both the most aggravating and comforting part of a founder’s journey. It only takes one “yes” to change everything, but getting there often means facing a mountain of “no’s.” Not every founder has the resilience to push through the rejection, but those who do often find success right when they’re ready to give up. In today’s episode, I chat with Christal Wang, co-founder and CEO of Shimmer, the top ADHD coaching platform for adults. Christal shares her journey from YC to closing a successful pre-seed round, and how she navigated the challenges of raising a $2.2M seed round after a major pivot. We dive into the emotional toll of fundraising, the importance of perseverance, and how a single “yes” can make every rejection worthwhile.

In this episode, we explore the realities of fundraising with Orri Bogdan, Founder and CEO of VAE Labs. Like many founders before him, Orri’s journey to raising a $2M seed round was fraught with challenges. From losing co-founders to product failures and numerous rejections from VCs, Orri faced it all. Yet, he persevered by immersing himself in founder communities, forging connections, and eventually securing funding from Draper Associates. Orri’s story is a testament to the grit and determination required to succeed in the startup world. Before we hear Orri’s inspiring story of resilience and success, we’ll explore what led him to become the determined founder he is today.