The Lessons 5 Founders Learned Going From Startup to Growth Company

Written by Alton Zenon III
Published on Mar. 26, 2020
The Lessons 5 Founders Learned Going From Startup to Growth Company
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Not every idea is a good idea. For entrepreneurs in particular, sometimes pivoting away from a strategy that isn’t quite working is an important — yet tough — part of the journey in discovering what works best for the business.

“Be willing to walk away from something you put your sweat and tears into when the data is telling you that’s the right decision,” HealthJoy President and Co-founder Doug Morse-Schindler said.

Having a clear company vision and user base are often the foundation that support a leader’s next bright idea. Many founders across Chicago agree that taking risks and staying resolute as doubters voice their opinions are fundamental parts of building strategies that lead to a company’s success. Sean Harper, co-founder and CEO of home insurance provider Kin Insurance, said his company would never have grown to its current state had he listened to skeptics in his industry.

But an entrepreneur can’t evolve their business from startup to high-growth company by themselves: they need a talented team surrounding them. 


Doug Morse-Schindler
President and Co-founder • HealthJoy

Before Morse-Schindler and company Founder Justin Holland discovered a market fit for HealthJoy, they needed to craft a vision for the future of the company. Sometimes, a vision has to change in order for a business to be successful, however. What started as a direct-to-consumer business eventually transitioned into a SaaS-based enterprise. Morse-Schindler said fortitude through change was how he and his team reached success.


Key contributors to success: Identifying a segment of the market where our product fit really well and building a scalable go-to-market strategy were especially important. Once we had conviction in those two areas, it enabled us to invest more heavily in our sales and marketing spend to fuel growth. However, hypergrowth also meant that hiring the best talent and becoming operationally excellent became that much more important. 

Grit is one of the most vital values to embrace.”


Most important lessons learned: Grit is one of the most vital values to embrace before finding product market fit. Things will go wrong. You need to make sure your co-founder and executive team are able to row through the mud with you.

Don’t fall in love with your ideas or concepts. Be willing to walk away from something you put your sweat and tears into when the data is telling you that’s the right decision. Write down your mission, vision and values as early as possible, as they should be your primary framework of selling and evaluating the culture fit for new hires.


Ujjwal Gupta
co-founder • BenchPrep

When team members are treated well, they do good work. Keeping employees happy was instrumental to driving growth at the online learning platform BenchPrep, Co-founder Ujjwal Gupta said. 


Key contributors to success: Our people have been the most integral part of our growth and success. Co-founder Ashish Rangnekar and I quickly realized that we couldn’t continue to be involved in everything if we wanted to build a scalable, high-growth organization. So bringing in the right team at both the management and individual contributor levels and keeping them happy was imperative. 

Our people have been the most integral part of our growth and success.”


Most important lessons learned: Don’t be complacent. Once there’s measurable success, that’s the time to work even harder to replicate it and expand the operation. Customer focus is also critical. Several of the best enhancements that we incorporated into our product originated from discussions with existing customers. Make sure to listen to their needs because often, what they’re looking for is needed by many other potential customers as well. 

Lastly, recognize all professional relationships are a two-way street, just like in your personal life. If you are fair and do good by your people, they will keep their end of the bargain in difficult times. 


Tom Sosnoff
founder and co-CEO • IGNA | tasty

Who said leading a company can’t be fun? The founder and co-CEO of tastytrade, Tom Sosnoff, insists that entrepreneurs should let their passion for whatever they’re building motivate them; This motivation helps entrepreneurs tune out negative voices and have fun along their company’s growth journey. 


Key contributors to success: Growth is a by-product of confidence, passion and bringing on people who want to be challenged. Success requires taking risks and we took risks every chance we could. 

Internally, we focused on free cash flow and building a strong revenue model. Externally, we were all about our customers. These factors allowed us to prove our concept, grow our skill set and create a unique platform.

Make quick decisions and take plenty of risks.”


Most important lessons learned: The foundational keys to building a great business really never change. Success is all about building on an idea that’s based on a clear vision. Never try to solve a problem or fill a need. Never listen to anybody, and just have fun. Articulate your model and your passion. Display extraordinary domain know-how. And most importantly, make quick decisions and take plenty of risks. 


Sean Harper
CEO and Co-founder • Kin Insurance

Nothing is ever 100 percent perfect, and this is a fact Harper focuses on as he grows Kin Insurance. Keeping an open mind and being receptive to change at a growing company can lead to unforeseen wins, Harper said. 


Key contributors to success: Opportunity was the biggest factor in Kin’s growth. The company was built from the ground up on modern software so that we could expand faster and develop new products quickly. We began in 2016 as a virtual brokerage. But we wanted to move faster, so we raised $47 million in funding to form our own insurance carrier and launched it in August 2019.

When approaching a problem without preconceived notions, it’s possible to come up with incredible insights.”


Most important lessons learned: I always try to keep a “beginner’s mind” so that I don’t assume that anything can’t be changed. When approaching a problem without any preconceived notions, it’s possible to come up with incredible insights. 

If we listened to industry doubters who said there was no way to automate homeowners insurance — that no one would shop for home insurance online or that regulators would never trust a tech company to run an insurance carrier — we wouldn’t have taken the necessary chances to get us where we are today.


Eduardo Vilar
Founder and CEO • Returnly

When scaling, Returnly Founder and CEO Eduardo Vilar focuses on hiring individuals with more than raw talent: Vilar said their skills should be aligned with the values and vision of the company. Vilar added that opening new offices in other cities around the world furthered the company’s ability to hire for diversity, as well as alignment.


Key contributors to success: In the early stages, it was crucial for us to remain a customer-first and family-friendly company. By providing an effective product and building a place where our employees enjoy working together, we have been able to create a strong foundation for our growing company. 

A major milestone was opening our offices in Chicago and Madrid, in addition to our San Francisco headquarters. By expanding our operations in these cities, we’ve been able to tap into a diverse pool of talent and hire the best people for the future of online commerce.

Alignment around our company values has helped us successfully hire at scale.”


Most important lessons learned: The importance of defining values early. Of course, talent and skill are critical. But we look for other traits as well, like having an entrepreneurial mindset, curiosity and lack of ego. Alignment around our company values has helped us successfully hire at scale, taking us from startup to growth-stage business. 

Across every department, we work to keep a unified culture of collaboration and openness. Having a global team with different backgrounds and experiences has given us the ability to creatively find solutions for modern day e-commerce problems.


Responses have been edited for length and clarity. Images via listed companies.

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