12 Things I Learned Working at Uber, Instawork and Intro

My entrepreneurial journey began when I was 12. I decided to take a shot at greatness with Shovel Squad, a snow removal business in the suburbs of Chicago, IL. I set out to make my mark in the world, and not only did it turn out to be quite lucrative (all cash mind you) but retention was through the roof.

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My experience with Shovel Squad at such a young age gave me the confidence to push myself to gain new experiences and knowledge. Over the years, I have been fortunate to work at Uber, Instawork, and now Intro, where I am the Head of Business Operations. Each new job has helped me evolve into the entrepreneur I am today, and I’d like to share with you all the lessons that have shaped my professional journey.

So, let’s get into it.

1. Integrity first

Operate with strong morals. You can be intelligent, hardworking, and also humble. Brilliant jerks might deliver short-term results, but crush long-term culture. Be honest and never fudge your metrics.

2. Time is a finite resource

Just because someone asked you to do something, it doesn’t mean you should. Remember that for every request you say “yes” to, you’re saying “no” to something else. Is that trade-off worth it?

Related: Book a one-on-one video call with top business leaders

3. Be adaptable and positive

Startups change. All. The. Time. You need to be willing to pivot to higher-impact work. Sometimes you learn you are sprinting straight in the wrong direction and need to turn around. Learn to disagree and commit. Don’t be afraid to kill your baby.

4. Close the loop

Don’t wait for people to follow up (that goes for peers and managers). When you commit to something, write it down. If you can’t follow through on your commitment, communicate early and tell them why. Be proactive.

5. 10x yourself

If you are getting paid $150k, how do you deliver value in excess of $1.5m? $15m? How do you automate 20% or even 80% of your current workload to focus on higher-impact projects? Impact is everything.

6. Handcraft, first. Scale, second.

Don’t obsess over scaling an initiative before you know if it works. Test your hypothesis in a small and controlled manner to prove the impact.

Handcrafted: The founders of Airbnb took photos of the first listings in NYC

Scaled: Airbnb builds user flow to upload listing photos with best practices

If it works; then, break your back to scale!

Related: 12 Ways Entrepreneurs Can Sharpen Their Leadership Skills

7. Keep things simple and execute

Don’t overcomplicate things.

Distill your big vision into stages, break those stages into groups of smaller tasks, and start executing. It’s better to make 10 decisions per day with 80% accuracy instead of 2 decisions per day with 100% accuracy.

Move fast.

8. Own your metrics

You should know your OKRs and all sub-metrics.

If this doesn’t come naturally to you, I recommend taking out a piece of paper and physically writing down your metrics every morning and afternoon (I did this and it helped tremendously).

It is absolutely critical to spot when things are moving in the wrong direction.

9. Make some magic

Obsess over your customers. Deliver insane value so they want to shout on the rooftop about you. You need customers to refer two people, that refer two people, that refer two people, and so on. Referrals are critical for exponential growth.

10. Constraint breeds creativity

Imagine you had 1/10th of your budget. What can you accomplish? What automation can you build to avoid the extra hire? What skill can you pick up on Youtube? How do you do more with less?

Every dollar invested is a dollar you need to pay back.

Related: 6 Habits of Effective Entrepreneurial Leadership

11. Always be learning

What you did to get to this point does not guarantee your future success.

Go deeper into your function or expand your breadth of skills. Find podcasts, Youtube channels, Medium articles, Substack blogs, and mentors that will help you grow. Reinvent yourself constantly.

12. Hustle hard and laugh often

Tragically, some of my teammates passed away from freak accidents and terminal illnesses. I’ll never forget them and am so grateful for my time with them. All of our days on this planet are numbered. If you are going to spend 8-12 hours per day working… don’t waste it. Do great work and treat people well. And have some fun.