Aaron Steffey of Propeller Bonds On 5 Things You Need To Know To Successfully Scale Your Business

Authority Magazine Editorial Staff
Authority Magazine
Published in
7 min readFeb 1, 2023


Your product is NOT perfect. Your product is not perfect upon its launch. You will need to launch, and iterate again, and again, and again. The product you launch will not look like the product several years later. Get a minimum viable product to market and figure out what works.

Startups usually start with a small cohort of close colleagues. But what happens when you add a bunch of new people into this close cohort? How do you maintain the company culture? In addition, what is needed to successfully scale a business to increase market share or to increase offerings? How can a small startup grow successfully to a midsize and then large company? To address these questions, we are talking to successful business leaders who can share stories and insights from their experiences about the “5 Things You Need To Know To Successfully Scale Your Business”. As a part of this series, we had the distinct pleasure of interviewing Aaron Steffey.

Aaron Steffey is from Philadelphia, Pennsylvania and is the Co-Founder and Co-CEO for Propeller Bonds — a company with a goal to simplify, automate, and distribute surety bonds more efficiently for agents and carriers. In his role, he is responsible for the company’s strategy, fundraising, and growth efforts. Steffey began his career as a managing partner for his family’s Indianapolis-based insurance firm, Steffey Insurance Agency, and holds an MBA from Villanova University.

Thank you for joining us in this interview series. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’?

I live in Philadelphia with my wife and three kids (Quinn, Callan, and Liam). I grew up surrounded by insurance as my parents ran a small insurance agency. My grandfather owned a steakhouse in the area, so I come from entrepreneurial stock and have always seen the working world through that lens. I completed my undergraduate studies at Ole Miss and launched Propeller with my cousin Chris Kolger shortly after finishing my MBA at Villanova. When I’m not working, I enjoy socializing with friends and family, rooting for Philly sports, and raising money for the Ireland Funds.

You’ve had a remarkable career journey. Can you highlight a key decision in your career that helped you get to where you are today?

There are many decisions that all build on one another, but I’d say the overarching decision I made in my life that has helped me the most is focusing on networking. That means building a network, extending my network to others, and meeting people from all walks of life and career backgrounds. I’m genuinely interested in learning from others, and I love socializing, so it came naturally and has always really paid dividends for me.

What’s the most impactful initiative you’ve led that you’re particularly proud of?

Probably establishing and executing the distribution strategy behind Propeller. Our distribution strategy is completely unique to the industry, in my opinion, and forming our partnerships that we have and how we went about scaling our distribution. I’m very proud of that today.

Sometimes our mistakes can be our greatest teachers. Can you share a mistake you’ve made and the lesson you took away from it?

Extending myself too far is probably my biggest mistake I continuously make, but I’m getting better at it each day. I genuinely want to be present and available for everyone, but sometimes in doing that, I bite off more than I can chew and fear letting people down. I’ve learned that setting expectations for yourself and others is extremely valuable and that people are generally pretty understanding if you level set with them in the beginning.

How has mentorship played a role in your career, whether receiving mentorship or offering it to others?

My biggest mentors in business are my parents. They taught me hard work as I watched both of them work tirelessly on their agency. Now, I consider several of our investors to be mentors, and it’s been great to receive perspectives from different personalities. In a rapidly growing company, you’re drinking out of a firehose continuously. It’s nice to have people around you that have been there and done it before. Some of our employees have reached out to me for mentorship, which is very flattering. I just keep a standing meeting with them where they can literally ask me anything about work, life, or whatever they want, and I’ll give them my best advice. It’s a cool opportunity, and mentorship strengthens your relationships overall.

Developing your leadership style takes time and practice. Who do you model your leadership style after? What are some key character traits you try to emulate?

I’m not sure I have a model for my leadership style. Frankly, I’m still very much developing it and learning who I am and how to be effective and making mistakes along the way. I’d say the biggest thing I try to adhere to is being very transparent with our staff, our investors, and our partners. This builds trust with everyone and allows everyone to feel like they know where this company is going and understand my desired outcome along the way.

Thank you for sharing that with us. Let’s talk about scaling a business from a small startup to a midsize and then large company. Based on your experience, can you share with our readers the “5 Things You Need To Know To Successfully Scale Your Business”? Please give a story or example for each.

  • Your product is NOT perfect. Your product is not perfect upon its launch. You will need to launch, and iterate again, and again, and again. The product you launch will not look like the product several years later. Get a minimum viable product to market and figure out what works.
  • Distribution and sales are king. You need early revenue to keep the company alive to improve your product and offering. You’ll also need revenue if you intend to raise money. Focus on hitting this hard in the very early days.
  • Don’t bootstrap too long. Some companies tend to bootstrap or delay raising money too long for fear of over-diluting the company too early. While this is certainly possible, and you want to nail it just right, raising money to gain market share and distribution quickly is usually worth it.
  • Nail your first hires. I cannot stress this enough. It is extremely difficult and exhausting to have to move away from bad hiring decisions in the early stages of the company. Conversely, hiring rockstar performers that have equity will make your life so much easier as the company scales and grows. These early decisions are super critical. They will become part of your management team.
  • Get organized. Early on, the business can be a bit of a mess, but as you scale, it’s important to get organized. This means legal, accounting, tax, insurance, employee procedures, etc. All that stuff will come into play as you scale into being a “real” company and getting your arms around it early on will help as you grow.

Can you share a few of the mistakes that companies make when they try to scale a business? What would you suggest to address those errors?

The biggest mistake is not taking time to step away from the day-to-day grind and work on the business as opposed to in the business. When a company starts to take off, you are just trying to ride that momentum wave and grow as much as possible and hire as fast as possible, but sometimes taking a step back and asking yourself simple questions, like “is this the best hire or is it just convenient?” or “do we need to implement technology to help us scale more efficiently?” Or even taking the time to assess if it’s sustainable. You can get caught up in it and lose sight of the overarching vision of the company.

Scaling includes bringing new people into the organization. How can a company preserve its company culture and ethos when new people are brought in?

It helps to include your model employees in the hiring process. Allowing your key people that you’d love to replicate or emulate in your company in the hiring process gives the company a much better chance of hiring additional staff that reflects those same qualities and strengths.

Many times, a key aspect of scaling your business is scaling your team’s knowledge and internal procedures. What tools or techniques have helped your teams be successful at scaling internally?

The tools we have invested in are more to facilitate speed and efficiency as opposed to knowledge. For the knowledge base, we just do a lot of good old-fashioned shadowing. When new hires come on, they are encouraged to sit in on as many demos as possible and come to every meeting possible. We keep that very encouraged, and it helps get our folks up and running quickly.

What software or tools do you recommend to help onboard new hires?

From a purely HR standpoint, we use Justworks to onboard all our employees. They house the entire employee onboarding experience for us.

Because of your role, you are a person of significant influence. If you could inspire a movement that would bring the most amount of good to the most people, what would that be? You never know what your ideas can trigger.

It sounds cliché’, but I’d love for everyone to find something they are really good at doing, and enjoy doing, and do that for a living. Life is too short to go to work every day at a job you hate. Launching Propeller has been so liberating for me, and I genuinely love it. I wish everyone could have this experience. Happiness levels would increase dramatically.

How can our readers further follow your work online?

I don’t participate in social media other than LinkedIn. I love LinkedIn and think it’s such a fascinating place to be and due to my love of networking, it’s the perfect place for me to allocate some of my time. For more information about Propeller Bonds, visit www.propellerbonds.com.

This was truly meaningful! Thank you so much for your time and for sharing your expertise!