Upstart's Culture of Entrepreneurship by Jenna Abdou


Organizational culture expert Scott Crabtree cites that our life circumstances make up less than 10% of our happiness. It’s the way we cope with them that matters. 

Thus when online lending platform Upstart embarked on Project Fast and Furious - their pivot from income share agreements to loans - the way their team “buckled down and did it” enabled them to navigate the three-month sprint without losing a single team member. 


Since making the decision in 2014, Upstart borrowers went from loaning a total of $3 million in the organization’s history, to $180 million in loan originations today. 

According to Co-founder and Head of Operations Anna Counselman, the key to Upstart’s adaptability and execution is a self-sustaining culture. 



We strive to build a culture of entrepreneurship. It’s not the type of culture where you go and tell your manager to fix it for you. It’s a self-sustaining business where everyone is constantly looking to make things better.

“When you empower individuals in this way, you’re always going to be surprised by what they deliver,’ she continued. 

As with everything in business and life, you can’t just say it. You have to live it. 

Here’s how they do it at Upstart. 

Build a team of initiators. 

“We ask everyone to always question the status quo. If you see an opportunity flag it, tell someone, or add it to our running wish list of product improvements,” Anna said. 

At Upstart, team members are encouraged to go to the product team first. 

Most problems should get solved on the product level before they become operational problems.

Developing innate collaboration between departments implements a tight feedback loop, leading to fast execution.

It’s equally motivating for team members when they can see tangible improvements made to the product. 

To take it a step further, the feedback loop creates a “self-cleaning mechanism of improvement” and the gratification reinforces the process. 

Balance speed and sustainability. 

“Speed isn’t about making people work crazy hard all the time,” Anna explained. 

Instead, you should embolden people to make fast decisions. By quickly removing roadblocks you’ll empower them to make judgment calls, move forward, and iterate. 

While Facebook’s mantra “Move fast and break things,” set the standard for speed at startups, it’s important to remember that you won’t be sprinting forever. 

There are moments “when everyone is sprinting really hard with super aggressive timelines and burning the midnight oil. They come in spurts, and then you have a lull with breathing room,” Anna expressed. 

Onboard for success. 

Especially for scaling organizations, it’s critical that new hires are successfully welcomed to the team and have a clear understanding of your company culture. 

Demonstrate your culture of entrepreneurship by explaining to new team members, and reinforcing to currents ones, that if they find a problem they should actively work to solve it.

No matter how small, you should think of every opportunity as a chance to prove how good you are.

As a founder or team leader, it’s vital to uniquely celebrate each team member’s contributions and provide opportunities for them to advance in the organization.

Anna suggests working one-on-one with team members to understand their goals. Having a personal relationship with each member of your team enables you to show gratitude in a way that resonates with them, as well as provide new opportunities that are in line with their career path.

It’s not a one size fits all approach. As a manager, you need to tailor it to the right person.

Acknowledging and rewarding individuals in the way that resonates with them not only inspires their future behavior, it empowers them to be champions of change for the rest of the team to follow. 

Show don’t tell. 

In addition to creating a self-sustaining product, developing a culture of entrepreneurship enables team members to look to their partners and exercise the same initiator’s mentality. 

“You can’t say ‘I want the company to be nimble,’ and then have it be nimble,” Anna affirmed. 

“You have to set an example. You have to act nimble. You have to make fast decisions. You have to launch things quickly. You can’t build consensus forever before moving forward,” she continued. 

We ask our employees to be the change they want to see.

Stay scrappy through scale.

At the year’s close, Upstart is set to be over 100 team members. For Anna and her co-founders Dave Girouard and Paul Gu, their highest goal is to maintain their culture as the company grows. 



Follow these three principles to cultivate a cohesive and collaborative culture through scale. 

  1. Hire the right team members. Translation: You want ‘Get shit done’ kind of people.  
  2. Ask those people to maintain the culture - You can’t be what you can’t see. 
  3. “Be vigilant about fighting bureaucracy!” Don't let decision-making committees and rigid processes override your culture of entrepreneurship. 

To gain deeper insight into the culture powering Upstart tune into Anna’s Beyond the Headline interview and follow the team on Twitter here.


Images retrieved from Upstart.



Further Reading
  • How MeUndies Made Merchandising Their Competitive Advantage — When MeUndies thinks about their underwear subscription service they compare themselves to Netflix. What the streaming pioneer did for TV, the Los Angeles startup wants to do to your underwear drawer. The goal is to provide monthly subscribers with the staples they love while delivering elements of surprise - Think briefs with donuts and dinosaurs - right to your doorstep.
  • Seedling Relies on Childhood Curiosity to Inspire a Creative Team — On a recent flight home, I spent over an hour browsing a children’s play website, completely enamored by sets like Design Your Own Superhero Cape and Invent Your Own Insects. After sharing Seedling with everyone I know, despite few of my friends having children, I wondered why the brand struck a such a meaningful chord with me.
  • eero Designs Wi-Fi for the Smart Home Era — Nikhil Basu Trivedi, Principal at Shasta Ventures, recently distinguished exceptional founders by their ability to prioritize. “It all comes back to prioritization, speed, paranoia, and knowing that if you don’t iterate, even after finding product market fit, you can be disrupted by the next product,” he says.


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