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Lessons Learned from Founding Two Successful Startups

One of my favorite professional activities is mentoring fellow entrepreneurs, but to date, I’ve primarily focused on helping the local Austin tech community grow. As SailPoint has grown into a global company, I’ve embraced technology to enable a one-to-many connection with our team around the world, and have decided to take that same approach externally. With that in mind, I’ll be sharing a variety of advice, lessons learned and commentary about building a successful startup and entrepreneurship, and maybe a few other observations about life along the way. I hope you’ll join me on the journey.

As my first topic, it seemed fitting to look at the lessons I’ve learned after serving as a founder for two successful B2B startups (Waveset and SailPoint). Over time, this list will likely grow, but here are the primary lessons I share with new entrepreneurs who are starting out on a similar journey:

  • Focus on solving real customer problems. Before starting both businesses, my co-founders and I conducted market research, making a lot of cold calls to businesses to talk about the IT and security problems they were facing. This research led us to the opportunity of addressing identity management challenges for enterprise customers, a pain point we’re still working to alleviate 10 years later. Identifying a widespread problem that people would pay to solve was crucial in creating a successful business model.
  • Prioritize people and operational discipline. Another intentional choice we made across both companies was building a team of people we knew and trusted, including an experienced venture team to lead us in the right direction and further reduce our risk. Throughout this process, we made it a point to remain flexible and ground our decisions in operational discipline, which has been critical to our businesses as we’ve grown and scaled.
  • Build a culture that encourages teamwork. We knew culture would play a large role in our organization, especially when building and eventually expanding our team. We learned quickly to address culture misfits, even the high-performing ones (Netflix famously calls these “brilliant jerks”). While these people may bring incredible, innovative ideas to the table, they also bring disruption and instability to a company’s culture. We found that focusing on creating an environment where people feel appreciated and are “treated like adults,” all while having a great time at work, has ensured we continue to build a phenomenal team.
  • Define and stay true to your values. At SailPoint, our Core Values guide every decision we make from the top down. We live our values through how we treat our customers and employees, to how we build products and services, to our hiring and firing practices. As we’ve grown, we’ve come to realize that culture will evolve and change over time, but our core values remain our guiding principles. Ensuring that these values truly define how we work with each other, our partners, and our customers is what makes SailPoint unique.

The tech community talks a lot about breakfast tacos and beer bashes, but turning a startup into a profitable, market-leading company is harder than it looks. At SailPoint, we built a sustainable business on these foundational ideas, ultimately bringing us $100 million in revenue and record profitability 10 years later. Whether you’re just considering this entrepreneurial journey or already on the path, I’d encourage you to define and commit to a set of core values and key principles.  If you do, it will help you build a strong culture and, ultimately, a great company.

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