Rule 8: Sync startup and personal goals

Building a business is as much about architecting the right business plan as it is about aligning members of your team.

With three cofounders from different parts of the world and different cultures, we knew early on that vocalizing our personal goals would be a necessary component of unifying our leadership and strengthening our company.

In July 2014, we headed to San Francisco and did just that. One year after we met as summer students at Draper University, we gathered again in person to talk about our future.

We were deep in the trenches of wrapping up our minimum viable product (MVP) and navigating the disappointment of a key investor pulling his support. This investor was overreacting because of an unfounded rumor that I was leaving to complete my undergraduate engineering degree, and this uncertainty was only compounded by Allen and Sambhav (my cofounders) fearing that we were running out of capital.

By gathering in person, we could communicate clearly, dispel the rumors, distill the truth, and determine next steps in light of the unexpected challenges. We traded conference calls and boardrooms for a day at the beach. As we asked the big questions about our business, we also had to face some harsh personal realties.

At 22, I was at least four years younger than Sambhav and Allen. This age gap allowed me more flexibility in some ways, but more constraint in others. If I took a second leave of absence from Lehigh University in Pennsylvania, I was going all in on this startup and risking my ability to graduate.

Sambhav, from Hyderabad, India, was in a tenuous place with his visa status. He either had to return to Texas A&M as a full-time engineering graduate student or face likely deportation. Compounding these questions was the one certainty in his life, that like many young Indian Hindus, he had an arranged marriage set for 2016.

With a strong sense of family like many of his fellow Taiwanese, Allen felt he should return home to Taipei to be with his aging parents and long-time girlfriend. He was also concerned that he would tarnish his professional reputation if he did not complete the final year of his MBA program.

Our personal issues only added to the complexity of our nomadic work situation. After leaving Draper University’s coworking space at Hero City in San Mateo, we moved to San Francisco. We were the epitome of a scrappy startup, juggling operations out of cafes, coworking spaces, and the apartments of benevolent friends.

There on the beach, we had an impassioned discussion to renew our original commitment. The pounding surf certainly bolstered my resolve, and, as I shared my vision, Allen and Sambhav resonated with renewed excitement. By asking honest questions, we could determine where we were, where we wanted to go, and why.

From those discussions, we each focused on these essential questions:

1) Where do I want to live?

2) What lifestyle (work, play or a combo) do I want?

3) What attributes do I want in the people that I work with in the future?

4) Do I want to take some time away from the startup world and reflect?

5) Do I want to go back to school to finish my academic work?

6) What are my financial goals?

7) What are my professional goals?

8) How do I want others to view me?

9) Am I in the startup game for money, fame, or solving world problems?

10) What are my three core personal values?

By finally asking these questions, we could stop operating in ignorance and make decisions from a place of clarity and understanding. Instead of assuming equal commitment and capacity, we capitalized on our differences. That day we embarked on a new Loopd path and resolved to do the following:

I would stay in San Francisco, fix the relationship with our upset investor, and begin taking part-time courses at local universities. I would assume responsibility for all business affairs as CEO including operations, finance, and fundraising and set up a headquarters office. I was also tasked with hiring hardware engineers, salespeople, and a marketing staff.

Sambhav resolved to work part-time for six months while he finished his master’s degree at Texas A&M. He would hire an immigration lawyer and return to San Francisco whenever possible.

Allen made the choice to return to Taipei where he could be less distracted by distant friends and family. From there, he would work full-time for Loopd and work to build a talented software group there.

While this separation was far from ideal, it seemed plausible with daily communication over Skype, email, Trello, and Jira, meetings in San Francisco every few months, and a strong commitment to our long-term product roadmap.

Looking back at that day on the beach, I realize now the profound inflection point it was in our business.

Perhaps by chance, we stumbled into a conversation about lifelong aspirations that unlocked a successful business partnership. Honest answers allowed us to build a viable roadmap regardless of cultural background, physical location, or personal obligations. With a healthy leadership team, we could then focus on building a dynamic company of talented individuals.

One of the several San Francisco coworking spaces that Brian worked out of while launching Loopd

Loopd cofounders at a beach near San Francisco in July 2014 setting their personal and company direction

I hope you enjoyed this preview to my new book Takeaways: Secret Truths from Leading a Startup. 

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