Tales of a Serial Entrepreneur (Part 5): How to Build a Safety Net When You’re Born Without One
This article is part of an on-going series. Read previous articles:
My freshman year of college, I looked around and thought to myself, “Where the hell are all the people who are like me? Where are the people who grew up as children of immigrants, in poverty, with English as a second language? And if they are like me, why are they the ones struggling most to succeed?” That was when I realized for the first time that I was fundamentally lucky. I may have grown up poor, but I was lucky to have a mom who read to me every night, to have grown up in a safe, affluent city, and to have gone to schools filled with children who came from extremely privileged backgrounds who knew about the SAT IIs when I had no clue.
My freshman year of college is when I decided to become an educator, because no child in the United States should have to be lucky.
Nine years later, I am now an educator and an entrepreneur. I take down systemic barriers to education innovation by building scalable solutions to systemic problems. I own my own business. I tutor, coach, teach. However, I came a hair’s breadth away from absolute disaster more than a couple of times. In 2013, my taxable income was $14,200 in a city where just my rent alone was ~$850/month. In 2014, things got so bad emotionally and mentally that I nearly moved back in with my parents instead of staying committed to my work in New York City. Again, I was fundamentally lucky. If I hadn’t saved money from previous jobs, I would have completely run out of money. If I hadn’t graduated from Princeton, it’s unlikely that I would have been able to earn $85-$100/hour tutoring students in order to supplement my then non-existent business income. If I had gotten sick during the six month period I did not have health insurance, I may have gone into debt. My parents would not have been able to help me. My dad is on disability and my mom was a prekindergarten teacher’s assistant who made less money per hour than I ever did, including the time my job consisted of washing dishes and mopping floors.*
I was lucky, but part of my success frankly comes from having taken risks without the benefit of realizing just how far I could have fallen. I now advise entrepreneurs to have money saved, to test their concepts on nights and weekends, to have their business validated before making it the sole source of their income. I also advise entrepreneurs to always have health insurance, no matter how dire their financial situations, because they need to protect themselves from a worst-case scenario of financial ruin following a medical catastrophe.
Some entrepreneurs are even luckier. They do not have to deal with what I had to deal with. They have parents with the financial ability to support them, family connections to successful business people who are happy to take them under their wing, access to brand-name schools no matter what the cost. Even more importantly, they’ve grown up steeped in the customs of power — how to self-promote, network, influence. Money and power twine together to create a safety net strong enough to allow entrepreneurs with this kind of luck to try whatever they’d like without fear of failure or financial and personal ruin.
While a part of me may wish that I had that safety net, I am now glad that I’ve experienced what I’ve experienced. Because of my background, I’ve learned how to build a safety net for myself, and by sharing how I did so, I hope to help other entrepreneurs from disadvantaged groups build their own safety nets as well.
We need people from the most disadvantaged backgrounds to have safety nets because we need entrepreneurs who are compelled to solve problems they themselves have experienced. Problems that, when solved, will lead to true liberation.
Step 1: Learn Obsessively
The ability to learn is a skill. If you trust in your ability to learn, when things invariably go wrong, you can pivot extremely quickly. It doesn’t matter what you do next, you know you’ll learn well enough to succeed.
Personally, I’ve left one job, been fired from another, and quit pursuing at least four different business ideas. However, I’ve felt confident each time because I knew that I didn’t need to stay when something wasn’t working. As Professor Deepak Molhotra says, “Quit early, quit often. […] I’m not saying quit something because it’s hard. I’m telling you to quit something because it sucks. It’s just not for you. […] If you have the opportunity, quit.”
You have the opportunity to quit only when you trust in your ability to quickly learn a new role.
Top Resources for Learning Obsessively
- The First 20 Hours: How to Learn Anything FAST by Josh Kaufman
- Books, Articles, and Videos that Change People’s Lives by Nexus Works on Pinterest
Step 2: Create Your Own Opportunities
I create opportunities out of thin air. I’ve sought out opportunities to take on projects, big and small, which have launched businesses, led to clients, and established strong, lasting relationships built upon other’s trust in my intentions and competence. I don’t wait for someone to ask me to do something — I see a need, propose the solution, do good work, and therefore create opportunities that lead to further opportunities.
I create opportunities out of thin air.
Go out and create your own.
Top Resources for Creating Your Own Opportunities
- This Is the Email You Send When You Want to Make an Impact, Do Good Work, Build Your Portfolio, and Advance Your Career by Deborah Chang
- The Briefcase Technique by Ramit Sethi
- The New Way to Work by Charlie Hoehn at TEDxCMU 2011
Step 3: Express Gratitude
Expressing gratitude is not only scientifically proven to make you a happier, more content person, it’s also one of the best ways to add value to your network. The people you’ve met, the owners of the “brains” you’ve “picked,” all they’re really asking for is for you to follow-up and let them know how their advice has changed your life. They will always remember your gratitude, which means they will always have your back. This is why I always go back to visit my teachers every year. My gratitude matters to them. And, when you express gratitude, that gratitude comes back to you in spades.
Top Resources for Expressing Gratitude
- Ramit’s definitive guide to building your network (with scripts), particularly “The Closing the Loop Technique”
Step 4: Build Communities
People fundamentally want to feel a sense of belonging. One of the best ways to feel belonging at scale is to be part of a community. This is true of both the personal and professional world. And once we feel like we belong to a community, we will not hesitate to help members of the community out, even if we don’t know them personally.
Communities can be built. Build communities so you build a safety net for yourself and for others. College graduates have local alumni communities, educators get together for Friday happy hours, I run #ClimbingCrew, a rotating community of folks who head out to a local rock climbing gym once a month. These are all examples of how simply inviting great people together to become friends, not connections, leads to amazing, reciprocal, and life-long relationships.
Top Resources for Building Communities
- The Best Networking “Hack” I’ve Ever Used by Brennan Dunn
- Communities Vs. Networks: To Which Do You Belong? by Brett & Kate McKay
Step 5: Get Health Insurance
This is not a joke. Get health insurance.
If you’re choosing between health insurance and rent, choose health insurance.
As an entrepreneur, you are always making tradeoffs to manage risk. According to best practices in risk management, you need to avoid catastrophic risk above all other risk. Getting so sick or injured that you require intensive, bankruptcy inducing medical care is a classic example of a catastrophe. Don’t risk it.
Top Resources for Health Insurance
- Saving Money on Health Insurance — See if you qualify for health insurance savings given your income level and family size.
- Catastrophic Health Plan — Lower monthly premiums for people under 30 with “hardship exemptions” that protect from very high medical costs.
Step 6: Understand Power
Power is the ability to act. Power is neutral. It is the imbalance of power, or the use of power for unjust ends, not power itself, that is the problem. And, just because you were not steeped in the customs of power does not mean that you cannot learn how it works.
Don’t play the power game. Do deal with people who play the power game.
My introduction to power began in the community organizing world, where I learned that there are three sources of power: positional power based on roles, financial power based on money, and relational power based on community. I choose to gain power purely through relational power. I never want power by fiat, I want power through love and trust. Because entrepreneurs who are from disadvantaged backgrounds are held down by systemic power structures that privilege one group over another, we need to be intimately familiar with how power works and be unabashed about building power to do good.
Top Resources for Understanding Power
- The 48 Laws of Power by Robert Greene and Joost Elffers
Step 7: Specialize
When you specialize, you become irreplaceable. I say I grow expertise in only three areas: education, scalable solutions, and human behavior. I doubt there’s anyone else in the world who can do exactly what I can do, and that’s precisely what makes me valuable.
However, I didn’t always know that this is what I would do. Instead, I tested a bunch of different roles and projects, checked in with my gut to see what I was interested in, and one day I just knew.
Top Resources for Specializing
While I acknowledge that taking these steps is hard work, and you may bemoan the fact that you weren’t born into some types of privilege, you don’t have to be born with a safety net in order to build one. Turn your perceived liabilities into strengths:
- Did you grow up poor? Empathize with the plight of other people who also grew up in poverty to solve problems that are truly worth solving.
- Are you a woman or a person of color? Access specific opportunities geared to supporting you.
- Did you or your parents immigrate to your country? Your second language, your cultural practices — they help you challenge assumptions and make out of the box connections.
- Are you differently abled? If you build to meet your own needs, then you’re also building to meet the needs of others. Designing for the outliers leads to designing for the masses.
When you know how to create a safety net for yourself, work to build safety nets for others as well. Mentor, not just those who remind yourself of you, but those who are different, particularly those who have been underserved — women, people of color, from poor backgrounds, differently abled, immigrants. Support organizations that are geared towards creating opportunity for all.
As entrepreneurs, we take on immense risk. We do so because we believe in solving problems that have no known solutions. Therefore, we are uniquely positioned to catch each other when we fall. Let us be each other’s safety nets.**
*One day, I intend to work on a project that will lead to paying all prekindergarten teachers at least $150,000 a year – at least. That, alas, is a project for another day.
**For a list of organizations I’ve personally experienced building safety nets at scale, please see: To Whom I Owe the Greatest Gratitude by Deborah Chang
Do you have a story or piece of advice you’d like to share with startup founders?