Sonia Steinway

Be intentional. Carve out time at the beginning of every week and every day to plan and prioritize your time.


Sonia is the co-founder and president of Outside Financial. Her passion is helping people make sense of their financial lives. Before founding Outside Financial, Sonia worked as a consultant for Bain and Promontory Financial, and clerked for Chief Judge Katzmann of the 2nd Circuit Court of Appeals and Chief Justice Strine of the Delaware Supreme Court. She has published several articles on consumer finance, and is regularly quoted as an industry expert on auto finance. Sonia received a BA from UPenn, summa cum laude, and a JD from Yale Law School.

Where did the idea for your company come from?

Almost all Americans own cars, but almost no one likes the process to buy or pay for them. I’ve certainly been to the dealership’s “back office” and left feeling confused, frustrated, and taken advantage of. My co-founder, Jon, was an investor in public auto dealerships, and realized that they were making more of their money selling financing than they were selling cars. He believed this was bad for consumers as well as a bad business model long-term, and he determined to do something about it. He needed someone with a legal and business consulting background to help create the business model and launch the company, which is where I came in.

What does your typical day look like and how do you make it productive?

I’m sure every entrepreneur will say that there’s no such thing as a typical day, but there are some common themes. All of our customers are on the East Coast, so I start my day early (5:30 AM PT), following up on any customer questions or complaints, checking our social media accounts, and perusing auto finance news to see if there is anything new or interesting. We have a daily team scrum call from 8:45 – 9 to review our tech team’s progress and map out next steps. That also helps me to map out the rest of my day, whether that means calls with new potential or existing partners; team calls to plan for new features or troubleshoot issues; writing content for our site; creating video content for YouTube; or answering questions on Quora. I’m a hyper-organized person, so having a strict to do list makes a big difference for me.

How do you bring ideas to life?

I’ll use a current example: we’re creating a dashboard for administrators to understand where customers are in our process, both at an individual level and at a macro level. We know we generally need more visibility and data, and we’re figuring out exactly how to execute. Each member of the team (tech and business) is starting by brainstorming their own list of requirements and features, and identifying them as must-have or nice-to-have. Everyone will submit their list to me, and I’ll consolidate and roughly prioritize. Then we have a team web call scheduled to review that list (10 minutes), then walk through together to understand the time and resources necessary to execute on each item (40 minutes). Then we’ll decide together which member of our tech team will tackle each prioritized item (10 minutes). After the meeting, I’ll add tickets to Jira reflecting the discussion, and use our daily scrum calls to check in on progress and manage roadblocks, if any.

What’s one trend that excites you?

Growing numbers of car buyers are using direct lenders – that is, getting financing from their own bank or credit union, not financing arranged by the dealership. We created Outside Financial to educate car buyers and owners about their financing options, and our #1 tip is to secure financing before you car shop. We’re hoping that we can be part of that trend in encouraging buyers to go “outside” the dealership.

What is one habit of yours that makes you more productive as an entrepreneur?

I am rigorous about prioritizing my to dos at the start of every week (usually, Sunday evening). I try to set myself a series of goals for the week, and then do a smaller task review and goal setting session every morning. That helps me to make sure I’m spending most of my time on the most important tasks, and reserve some time for the kind of tasks that always pushed off because they’re not being pushed to the top of my inbox.

What advice would you give your younger self?

Launch a beta version faster. We thought that if we had everything buttoned up, we wouldn’t need to make changes when we launched. We were very, very wrong. The only way to know what customers want is to get in front of them. It’s much better to debut something and get feedback on it, then add in the bells and whistles that customers actually want, than to spend lots of time designing something for a mythical ideal customer.

Tell us something that’s true that almost nobody agrees with you on.

Reading contracts and legal disclosures is fun. (Sorry, I’m a lawyer; we have to feel like our work is appreciated!).

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Talk to my customers. My opinion is meaningless. They’re the ones who need my product (hopefully), so their opinions–about our colors, our logo, our process, etc.–are what matters.

What is one strategy that has helped you grow your business?

We’ve started using Upwork to find contractors, and it’s been a huge help in scaling our operations without having to worry about HR or major overhead.

What is one failure you had as an entrepreneur, and how did you overcome it?

We’ve heard a lot of “nos” from potential business development partners. Usually they’re polite, but it still stings when we think there’s a really good opportunity to work together. We try to keep all doors open, while at the same time prioritize other potential partners.

What is one business idea that you’re willing to give away to our readers?

I wish someone would create a better credit scoring alternative to Experian, Equifax, and Transunion. If you can do that, I think a lot of people would be grateful.

What is the best $100 you recently spent? What and why?

I recently hired someone from TaskRabbit to do a bunch of odd jobs in my house. It actually cost less than $100, and he managed to do a ton of tasks that I’ve needed to do but haven’t gotten around to for months, like changing the batteries in my smoke detectors and replacing water filters. I try not to think of my time in monetary terms because I’m worth more than that, but it can be a real burden to feel stretched in too many different directions.

What is one piece of software or a web service that helps you be productive?

As a team, we use Jira to keep track of our tickets. I think that works great for software/tech development, as long as we’re disciplined about creating and managing our tickets.

What is the one book that you recommend our community should read and why?

The Goal by Eliyahu Goldratt changed my life. It sets out a different way of thinking about optimizing process flows, and it works for big business decisions as well as personal time prioritization. It’s a really quick and easy read, and I recommend it to everyone.

What is your favorite quote?

A foolish consistency is the hobgoblin of little minds. (Ralph Waldo Emerson)

Key Learnings:

  • Be intentional. Carve out time at the beginning of every week and every day to plan and prioritize your time.
  • Be open. Your customers do know better than you what they need, and your job is to serve them, not to make the product that makes you (the entrepreneur) the happiest.
  • Delegate when you can. I’m still struggling with this one, but the more I’ve been able to ask for help, the more I free my own time to focus on the highest priorities.


Outside Financial: