Back in 2010, I tried to take shortcuts. I fabricated my resume with fake jobs, showcasing myself as a top performer in a sales role I never had. I flew from Hawaii to Los Angeles to interview for a role and ultimately received an offer for the job. But there was one issue – I couldn’t verify employment, I had zero references, and I had to bow out of the hiring process. I was embarrassed, humiliated, but committed to actually doing the work.
I took an entry-level sales position that taught me everything I needed to know about sales fundamentals. This role was a humbling experience, but it was crucial for building a solid foundation in sales.
In 2013, I broke into SaaS sales through sheer determination and a bit of clever maneuvering. I convinced a recruiter to believe in me enough to share the location of a mixer for new candidates, despite my resume lacking B2B experience. I shouldn’t have been there, but I showed up determined to win the opportunity.
Picture this: Two dozen candidates all fighting for face time with VP-level leadership. Two candidates at the bar see a VP across the room standing by himself. They take one last swig of their beer, look at each other, and race over to the VP for face time. This was what the event was like, and it was a blessing. My personality thrived in this type of environment, and I’m forever grateful to the recruiter who told me to go even though I wasn’t qualified on paper. By the end of the event, I won over leadership and ultimately received an offer for the job. Little did I know, the hard part hadn’t even started.
The Grind
They gave me an East Coast territory, meaning I had to work East Coast hours from San Francisco. This required me to be in the office at 6 am, which was 9 am on the East Coast. At the time, I lived in East Bay, Northern California, specifically Brentwood, and it made my commute to the office a living hell for MONTHS. I had to wake up at 3 am, leave the house by 3:30 am, and catch the first BART train out of Pittsburgh at 4 am to be at the office by 6 am. Even then, I was 15 minutes late every day because of the unreliable shuttle I had to take once I landed in SF.
The Dedication
Despite the challenges, I never complained, never whined, and never asked for my territory to be changed. I embraced it with a smile, knowing this was a life-changing opportunity. I was working for one of the biggest tech companies on the planet. This was my shot. Many would have passed on such a demanding role, but I knew that if I could hang in there and perform at a high level, it would change my life forever.
The Results
Fast forward to today, I’ve been the top seller at three startups, been part of a Google acquisition as a leader, and now I’m a senior leader at a startup ranked #5 on the Forbes Cloud 100. I don’t say any of this to brag. The point is: There is no elevator to success; we all take the stairs. The journey is tough, and sometimes, you’ll have to eat shit to make your dreams a reality.
The process was humbling, but it was also the foundation of my success. By embracing the stairs, I built a career grounded in real experience and genuine accomplishments.
Lessons From The Stairs
Don’t Let Your Ego Block Your Blessings: When we’re fighting for our dreams, there is no easy button. In the words of Gary Vee, we all have to eat a little shit – humble yourself and get to work. Success requires dedication and the willingness to embrace the grind.
Don’t Compare Yourself to Others: As you see peers around you succeeding, remind yourself that it’s not you vs. them; it’s you vs. you. Your journey is your journey. Your road to success is paved perfectly for YOU. Everything you need for longevity is built into the process, so EMBRACE it. If your journey looks vastly different from theirs, it’s okay. Everyone takes the stairs at some point, so don’t be hard on yourself if your path starts out a bit different. You’ll be better because of it.
Your Turn
Are you curious what the “stairs” might look like for YOU in this chapter of your life?
Do you believe you were destined for something MORE but you’re a bit stuck on what to do next?
Let’s embrace the stairs together – you don’t have to go at it alone.
Book a complimentary call here so we can get clear, create a plan, and start climbing!







