I Just Got Started: Early Lessons from My Entrepreneurial Journey

Jason Roberts
Village Up San Diego
3 min readFeb 11, 2021

After a 20-year stint moving up the corporate ladder, I finally decided it was time to start my own company. While I won’t get into my motivations for making the leap, I felt that being a Black executive in Corporate America prepared me well for entrepreneurship. Over the years, I had to develop the mental fortitude and thick skin necessary to push through skepticism and sometimes even exclusion in the workplace. The constant need to prove one’s self fueled my climb and my development. From leading strategic initiatives across various departments and disciplines, to eventually running large P&Ls and frontline operations, I was able to build critical skills and experiences with each barrier I broke.

Yet, with one year under my belt as CEO of Frontline Careers, I now realize that a founder’s skills and experience alone do not equate to early stage success. Particularly, three specific survival lessons stand out: (1) have at least one trusted co-founder, (2) seek out others that identify with your mission, and (3) be honest with your own weaknesses so you can quickly address gaps before they become roadblocks to progress.

Lesson 1: Have at Least One Trusted Co-Founder

My biggest takeaway thus far in my entrepreneurial journey is that I would have already fallen short had I been a solo founder. Having a co-founder like Ari Malka, who not only compliments my skills and areas of expertise, but also disagrees with me, has been extremely valuable. He sees things I don’t, and I see things he doesn’t, but we both aim to learn from these experiences. Without this balance, this venture would be that much more challenging and potentially over by now. So for any entrepreneur starting out, I highly advise against going it alone. Find at least one co-founder who compliments your skills and is aligned with you on the mission and purpose of your company.

Lesson 2: Seek Out Others that Identify with Your Mission

Your mission says a lot about your company, sometimes more than you think. To my surprise, people I have met for the first time are more willing and eager to open doors for me than some I have known for years. Why? Because they too believe deeply in our mission “to connect frontline workers who want more, with companies that offer more”. And, as a result, they want to help us without expectations of something in return. These Altruistic Networks as I call them, have already led to potential partnerships, customer introductions, support resources, and expert advice — all at zero cost. So as you set out, be sure to find a village of people that will support you, believe in your mission, and help you and your company grow.

Lesson 3: Be Honest with Your Own Weaknesses

Despite having a very complimentary co-founder, early-on I began to realize that we had gaps in our collective founder capabilities. More specifically, neither of us would consider ourselves project management experts, nor did we have the resources to hire that person as a bootstrapped startup. So instead, I turned to an executive coach I had used in my former corporate life for help. He quickly identified our gaps as a founding team, and helped us put in place processes to address and manage them. With his assistance, rather than struggle, we have been able to better leverage skill sets across our small but amazing team, and continually make progress towards key goals. The lesson? Be humble, self-reflect, acknowledge where you are not strong, and then seek help to fill the gaps.

Among other things, your skills and experience as a founder are absolutely critical to long term success, and I do believe Corporate America is a great place to develop them. Still, in the early going of my entrepreneurial journey, I have found that having a strong and complimentary co-founder, connecting with people who believe in my company’s mission, and being honest and vulnerable about my own weaknesses, is extremely important, too. Of course, our success is far from guaranteed, but I do believe recognizing these early lessons has improved our chances. Hopefully you find them helpful, too.

--

--

Jason Roberts
Village Up San Diego

Jason Roberts is CEO and Co-Founder at Frontline Careers — a tech startup that connects frontline workers looking for more, with companies that offer more.