1:48 - Fringe was founded with a vision to revolutionize employee benefits by delivering real value to our workforce. My background in financial planning revealed a significant gap: many employees lacked a full understanding and appreciation of traditional benefits like health and life insurance.

Our idea was simple yet innovative: provide benefits that address immediate needs, such as child and elder care services, streaming platforms, and meal delivery. We termed these offerings "lifestyle benefits," a concept that had been largely unexplored. Our goal was to offer these benefits at an affordable cost to employers while delivering high perceived value to employees, fostering goodwill and loyalty.

6:10 - The attorney I met in Richmond, Virginia had an eye-opening insight about entrepreneurs: we're not as risk-tolerant as we might think. He noted that our real fear isn't taking risks; it's having a boss. I could totally relate to that. I thought I was a fearless risk-taker, but it turns out I just couldn't stand the idea of working for someone else.

While running Greenhouse Money with Jason, things were going well. But then the concept of Fringe struck me like a lightning bolt. The potential of Fringe was enormous, and I couldn't ignore it. We tried to manage both businesses for a while because letting go of a reliable income is tough. However, after about a year and with some funds in the bank, I made the challenging decision to let go of Greenhouse Money. The idea behind Fringe was too powerful to ignore. It felt like the path to places I hadn't even dreamed of, and I had to pursue it.

9:35 - When it comes to partnering in business, I've learned some valuable lessons. Hiring employees is one thing – you look for talent and cultural fit based on shared values. As a business owner with four co-founders, trust is the cornerstone of our partnership

Our success at Fringe, I believe, is greatly attributed to the deep trust we have in each other. We've been through challenges like layoffs, and our response was marked by understanding and cooperation, rather than blame or infighting. This experience has fostered even more trust and communication within our company.

So, my advice is simple: if you're going into business with someone, trust them as deeply as you would your spouse or someone caring for your children because their decisions will significantly impact your life.

12:16 - When it comes to our company culture, I lead with the belief that most people don't want a boss, and they value flexibility, family, and trust. Our culture promotes unlimited paid time off, but we require everyone to take at least two weeks to prioritize rest and family over work. Our remote-first approach allows our team to choose where they work.

Our culture reflects my tendency not to praise excessively, as I grew up with my mom's praise for everything and my dad's constructive critique. As a result, our company may sometimes seem weak in recognition. It's a mirror of our habits, both good and flawed, and it teaches us more about ourselves than any other experience could.

To sum it up, building trust is essential in partnerships, remote work environments require mature team members, and your business is a reflection of your habits and flaws.

17:36 - I find it annoying when people obsess over what others are doing. My approach is to focus on our company's unique goals and not be swayed by the latest trends. I'm open to exploring new trends, but I don't buy into best practices arguments. I prefer to invent and lead the trend.

I keep a close eye on trends, pay attention to digital transformation, and utilize what's genuinely beneficial for our business. However, I avoid integrating digital transformation just for the sake of appearances or investor appeal. The key is to stay practical and useful.

23:27 - When it comes to raising funds, it's a challenging process. To maintain integrity and stay true to your vision, you must find investors who genuinely understand and believe in your business, not those who try to fit you into their trends or quotas. It's essential to interview potential investors as much as they interview you. You're the one with something valuable, and they need to invest their capital.

Avoid investors who solely focus on metrics and long-term plans that may not align with your business goals. The wrong investors can end up being like hiring your own boss. Don't settle for "dumb money" – look for smart, strategic investors who can provide more than just capital, they can bring expertise and insights that truly benefit your business.

27:52 - When interviewing VC firms, there are a few key factors you should focus on:

1. Fund Goals and Maturity: Understand the fund's objectives, its maturity, and the expected cash-out date. This will help you align your startup's goals with their investment horizon.

2. Investment Criteria: Ask about how they choose their investments. Ideally, you want to hear that they invest in founders and their perception of your potential rather than just the product. This ensures they're investing in you, not just your current offering.

These insights can help you find a VC firm that genuinely believes in your vision and is willing to support you over the long term.

31:17 - Finding the exact one person who has been through everything might be challenging, but learning from various mentors and drawing wisdom from multiple sources is a valuable approach. It's often not about getting a direct answer but gaining insights and guidance on how to find your own answers. Mentorship is indeed a multifaceted journey, and I'm glad to hear that you've been navigating it effectively. Please feel free to ask your next questions.

35:48 - It's all about the vitality of the business, which forms the bedrock for everything else. Sometimes, making difficult decisions becomes essential to guarantee the company's overall well-being. Imagine it as securing the oxygen supply for yourself before assisting others, much like the advice you hear on airplanes. It's not about obsessing over the bottom line but recognizing that if the business isn't robust, nothing else can thrive – not your role, not the clients who benefit from your work. Prioritizing the health of your enterprise doesn't mean you don't care about other stakeholders; it's a strategic step to ensure that you can effectively serve all parties, including the very clients, employees, and partners you're committed to supporting.

38:45 - The best advice I can offer to aspiring entrepreneurs is to let go of the idea of imitating others, especially well-known figures like Elon Musk, Mark Zuckerberg, or Steve Jobs. This hero-worship mentality might be fitting for children who are searching for role models, but as adults, we are already our own heroes. Here's why. We each possess a unique blend of skills, talents, abilities, and experiences that sets us apart from everyone else.

Ultimately, being a true entrepreneur involves embracing your individuality, being original, and conducting business in your unique way. It's about recognizing that you're already equipped with the tools for success. So, don't strive to be the next Zuckerberg; aim to be the best version of yourself.