13 Pieces Of Work Wisdom I Learned From Working At A Startup

by Chirag Sagar

There will be times when life seems to be closing all of its doors to leave us in darkness.

It's those times when, if we have the strength not to quit, we have the greatest opportunity to learn and grow.

When I faced that path in my life, I learned 13 of the most valuable lessons I still carry with me today. I lost what I thought was the most important thing to me.

I dedicated my life, energy and resources to growing a nonprofit that was the centerpiece of my life, Moneythink. Ultimately, I was asked to resign. I was crushed; ironically, however, it was the greatest gift I was ever offered.

I may not have been able to control my resignation, but I could decide what to do with my future, and that's where my learning began.

Let me give you a little backstory: Moneythink was my dream job. We spearheaded a movement of college students to transform the way high school students thought about, managed and used their money in the US. We were featured in Forbes, NBC and the Huffington Post, and slowly but steadily, we gained the support of major banks, CEOs of Fortune 500 companies and even President Obama.

Not only was I passionate about what we were doing, but also felt fulfilled building a startup from the ground up. Like any first hire for a startup, I was wearing many different hats, helping in any way possible.

Eventually, I focused on streamlining operations and expanding the organization. However, we were growing so quickly, our goals, vision and mission were rapidly changing, too. It's a great thing for a healthy, developing organization, but I never imagined it would lead to my resignation.

Soon, I found we were at a juncture where my skills were no longer needed, and so, I was asked to resign from my position. The impact of this forced me to question and reassess my values, beliefs and character.

What would I do next? What did I want to accomplish with my life? What now?

It was the biggest blow I've faced to date. I spent nearly five years building the organization and, ultimately, was booted.

I consulted my friends who experienced similar situations and they provided me with great advice to help me move forward. Within two days, I convinced myself to leave on good terms, get back on my feet and push my way through this. Sulking wouldn't help anything and had no place in my future.

Today, a year later, I'm still great friends with many members of the Moneythink team. If I hadn't forced myself to rise to the challenge, I could have lost all those valuable friendships and connections.

The world didn’t stop for me. My only option was to get back on the horse and continue my journey, or get left behind. Life progressed forward and the only thing I could do was take everything that happened and use it as a learning experience.

Viewing my experience through this lens, I eventually stopped feeling sorry for myself and instead, reassessed everything I learned from my time at Moneythink.

Here are the 13 lessons I learned that you should know:

Treat the nonprofit as a for-profit.

Stay lean, conserve funds and time, recruit top talent, document and build efficient, effective and automated work processes, think systematically, delegate where appropriate, strategize then execute, learn from mistakes, improve and call out the BS.

With no direct source of income (which holds true for many nonprofits), it’s imperative to optimize time, money and energy. At Moneythink, we treated deadlines and goals like any for-profit entity would.

Embrace fear, then conquer it.

I was building a new company in a new city. It was scary. I didn’t have many friends, I lived near the south side of Chicago without a car and was underpaid the first few months because we didn’t have enough money to pay ourselves a full salary.

I verbally took the leap and committed to go full-time with Moneythink, whether their CEO liked it or not. Backing out wasn’t an option.

As the Aztecs burned their boats in the 1500s to conquer the Inca, I, too, burned my bridges and options to go full-time with Moneythink. As a result, I learned when I begin fearing, I’m stretching outside of my comfort zone and growing as a person.

In accepting and acknowledging fear and having the courage to move forward, therein lies growth and new possibilities.

Accept and learn from constructive criticism, but be wary of accepting advice from many.

After every completed assignment, I immediately asked, “How could I have improved? What were the blind spots? Did I miss anything?”

Our team would ask each other this, as well as people more experienced than us. From day one in the office, whenever I’d make a mistake (i.e. a typo in an email) and a colleague noticed it, they’d call me out on it.

However, we learned most people have opinions on any matter when advice is asked, regardless of how useful that opinion may ultimately be.

Over time, we learned to discern from whom to ask for advice and became wiser in choosing who to approach for counsel.

Assemble a personal board of advisors.

There were seven individuals I identified at different organizations with my exact role and job description. We’d share the best practices with each other.

Several of these organizations have existed for more than 15 years. I’d be a fool to not learn from their mistakes and emulate what they claim works best. I’d begin the relationship by giving something and then asking for something in return.

The reciprocity continuously flowed back and forth, and we continued to share the best recruiting, interview, training, on-boarding and systemizing practices with each other.

Seek mentors.

Slightly different than my personal board of advisors, my mentors were individuals I identified as people I could see myself becoming one day.

Some were several years older and others were decades older. Building a relationship with and keeping them in the loop on my life provided me opportunities to ask them for specific advice that no one else could provide when the time called for it.

They had lived through the scenarios I experienced.

When I parted ways with Moneythink, I called three mentors to ask them about their experiences when they were booted from their companies and how they moved forward. I built a personal relationship with all three of them and they held me accountable.

Pursue excellence.

Perfection is asymptotic; it can’t be reached, but you can get close. I marketed Moneythink’s internship opportunities by learning from my peers, Googling and experimenting.

Our team continuously documented everything. We measured and tracked everything we did so we could improve.

I tried improving on this process and assigned an intern to assist in identifying marketing channels to amplify our search results the next time around.

The intern would spend his or her time researching, interviewing and learning from the best HR companies. We wanted to be the best we could be, which brings me to my next point.

Build systems, automate and delegate for growth.

Moneythink envisions a world in which every teenager, regardless of background, enters adulthood equipped with the knowledge, skills and tools to navigate the financial challenges of the real world.

Accomplishing this grand vision required consistent, high-quality programming and scale.

The goal was to build an organization that had standardized protocols and work processes and, thus, freed up our time to focus on other tasks that required more creativity.

We brought on interns to work through the systems, while the full-time staff streamlined other work processes and oversaw their work.


When I wanted to learn about customer service, I picked up Disney’s “Be Our Guest.”

When I was curious about being a visionary, I read Steve Jobs' and Richard Branson’s biographies on how they started their companies. When I wanted to learn about marketing, I read a book by Seth Godin.

It’s the closest way to tap into the minds of the smartest, brightest and hardest working people — alive or dead — uninterrupted.

Habits form work culture.

From day one at Moneythink, we hopped on a call every morning at 10 am to go over what we planned to accomplish for the day and to mention one thing that inspired us.

It was our 10-minute morning ritual. We also requested every person to respond to emails within 24 hours, even if the actual work assignment couldn’t be completed, to at least confirm receipt of the email.

These simple rules turned into habits, and are now ingrained in Moneythink’s work culture.

Humble hustle – grind with grit and build through resilience.

Moneythink was a startup. Some days required intense focus and concentration. Although I loved every minute of what I did and the impact I was able to make, at times, it was grueling and not fun.

One time, we ran a back-to-school fundraising campaign and were $3,000 short of the $10,000 mark.

With only 31 hours to spare in the campaign, I stationed myself at the nearest Dunkin Donuts and Facebook messaged more than 620 people to raise the remaining funds.

It was stressful, intense and one sleepless night. I took one 30-minute break and only consumed one Subway sandwich and a small coffee during the entire 31 hours. I was exhausted, but determined to succeed. And, I did.

We surpassed our goal by $1100. Sometimes, you have to bite the bullet and fight through the pain and exhaustion.

Environment matters.

Our office was located in University of Chicago’s Booth School of Business’ Polsky Center for Entrepreneurship.

Every day, we’d be surrounded by some of the brightest minds that the University of Chicago had to offer, and other entrepreneurs. Seeing others working on their ventures was uplifting.

We were able to bounce ideas off other entrepreneurs and immediately implement what we learned. If anything, our team learned we were “the average of the five people [we] spent the most time with.”

Vision and mission at the forefront, always!

If a decision being made did not align with the mission and vision of Moneythink, we didn’t move forward with it. With limited resources, time cannot be wasted. It’s that simple.

Accept. Forgive. Move on.

Considering the fact that we were only in our early 20s, I’d lose out on so much more from stopping friendships with the Moneythink team.

Just because it didn’t work for Moneythink doesn’t mean it can’t work ever again. Holding a grudge against anyone is exhausting and unhealthy.

I didn’t want to define this experience as an obstacle, but rather, as a stepping stone for my next endeavor.