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A Conversation with GoFundMe CEO Tim Cadogan

Imagine joining one of the most influential companies in the world a week before the COVID-19 pandemic hit. That’s the situation that faced Comparably CEO/Co-founder Jason Nazar’s recent guest for Entrepreneur and Comparably’s Leadership Lessons series: CEO Tim Cadogan of GoFundMe – the world’s largest online fundraising platform and one of TIME’s 100 Most Influential Companies of 2021.

“Start a GoFundMe” has become part of the everyday lexicon, with a donation made every second. Empowering people to give and receive help for important needs and dreams, the GoFundMe community has raised over $15 billion from more than 200 million donations from 190 countries. It has been at the center of giving for some of the biggest natural disasters and humanitarian crises, like COVID-19 and the racial equality movement. People turned to GoFundMe to help pay for everything from rent and food to small business support during COVID. And the Official George Floyd Memorial Fund received more than half a million donations.

The weight of having this kind of platform for everyday people to make an instant difference doesn’t go unnoticed by Cadogan. He takes the responsibility seriously and says it fuels his team’s purpose-driven work even more. One only needs to glance at Cadogan’s impressive background to know why he is the thought leader that he is. As a pioneer in advertising tech, he served as CEO of OpenX, as a Yahoo executive for the advertising and consumer search business, and as VP of Search at Overture. After earning his BS from the London School of Economics, an MPhil from Oxford University and an MBA from Stanford University, he honed his career chops as a consultant at The Boston Consulting Group and McKinsey.

Here are 13 valuable leadership lessons from Nazar’s discussion with this terrific chief executive:

1) Be reasonably unreasonable. If you are building something new and unheard of that is meant to fill a public need, you’re already doing something many would consider to be unrealistic or a pipe dream. Although rare for anyone to pull off “crazy unreasonable” and retain credibility, a CEO needs to have this kind of “reasonably unreasonable” mentality.

2) Paint a picture of a future that gets people excited. It is especially powerful when that vision is one of helping others. “There is nothing better than having a group of people around you, like family, friends and the community, to help you achieve that,” Cadogan says.

3) Consider three important questions as you decide what to work on. Do you work somewhere because of people you value? Do you work for your own interests? Do you do it for the money? “Ideally you’re hitting all three,” advises Cadogan. “But you will probably have to make some trade-offs.”

4) Taking care of employees should be core to the business. The week Cadogan took the reins of his new job, he made the early decision (March 5, 2020) to have everyone work from home due to the impending pandemic. He onboarded and met the team while learning the business remotely. As a result, the company is proud to support flexible working schedules for all employees, provide access to mental health and stress reduction resources, and robust wellness options.

5) Lead with purpose. The closer the alignment between an employee’s daily work with the purpose of the company, the more effective your team will be. Not only will this help your company be more purpose-driven and strategic, but it is also easier for individuals to focus and prioritize the right work that makes the biggest impact for the community.

6) Normalize asking for help as a leader. The desire to help others is a fundamental human truth: people are innately kind. They also want to be effective. People want to help others, yet it can be very difficult to be the one to ask for help. As a leader, Cadogan admits that he works to improve how he asks for help from his team, his board and the broader community.

7) Always remember the mantra “the next play.” Cadogan cites advice from Jeff Weiner that originated on the basketball court: “Whatever happens, good or bad, do a post-mortem and move on to the next play. Just keep cranking, there’s always more to do.” In other words, don’t waste too much time celebrating the wins or mourning the losses.

8) Keep an eye out for power curves and tailwinds.  “Whatever metaphor you want to use, be aware of the trends in society that have staying power,” Cadogan insists. Put yourself in industries that benefit from these tailwinds, and avoid businesses with unfavorable conditions where your brilliance may not make a difference.

9) Don’t be discouraged when your master plan has to change on a dime. A smooth ride to one’s goal is actually abnormal. There will always be plenty of things you don’t have control over, even as CEO. Those destabilizing events will inevitably occur, so adjust plans accordingly without losing confidence. Cadogan says these conditions are “normal state of affairs in business” and should not temper your ambition.

10) Leadership involves listening, writing, and co-editing. It is important to listen carefully to all the expertise across your team and synthesize what you’ve learned into notes with conclusions and decisions. Then share with your colleagues and co-edit to pool all your respective knowledge and thinking. Cadogan is a fan of Google Docs and believes that when used well, it can be a very powerful brain power multiplier.

11) Know your strengths and your weaknesses. It’s important to get a truly clear picture of yourself so that you can start making longer career arc choices wisely. Cadogan says his 30s were a time when the real gut check came in. He was more realistic about his own strengths and weaknesses, despite his ambitions.

12) Keep a few original and effective interview questions in your quiver. Cadogan thinks the traditional interview process is a very flawed and inexact way to determine what a candidate’s efficacy will be as an employee. Along with more expected interview questions, these are three that he likes to use to better determine the outcome:

  • “Can you walk me through a time when you faced a lot of adversity, and what you learned from it?”
  • “Have you gotten to where you are in your career thanks to smarts or hard work?”
  • “When during your career were you most happy and why?”

13) One benefit of working remotely is more direct communication. The old way of in-office collaboration often relied on making assumptions about other people based on body language and subtleties of language. That’s always been an imperfect method, so there is some benefit to the fact that a video conference demands clarity and over-communication.

For more from this hour-long conversation with Cadogan, watch the full webinar here. The growing collection of episodes from our series gives readers access to the best practices of successful CEOs from over 30 of the biggest brands, including Headspace, Zoom, Chipotle, and ZipRecruiter, to name a few.