Today's Entrepreneur


Today's Entrepreneur: Heath Silverman

Set regular, clear and measurable goals; Trust your instincts

Innovation series by Kristin Karaoglu
October 30, 2018
Short URL:

Today's entrepreneur is Heath Silverman, Co-founder and the CEO of Stessa. Stessa is a SaaS platform to track, manage, and communicate the performance of real estate assets. 
After nearly 20 years as a part-time real estate investor with a full-time job in the technology industry, Heath was inspired to build a scalable technology solution to streamline the entire real estate ownership lifecycle.  
Stessa launched today out of beta.


Prior to Stessa, Heath was Vice President, Worldwide Business Development and Marketing at Edmodo, the leading global education network.

A seasoned technology entrepreneur and executive, he has extensive background in developing and executing multinational strategies and formerly held positions in product, sales, and marketing across Amazon, Intel, and a number of technology startups.

Heath received a BA in Cognitive Science from UC Berkeley and an MBA with High Distinction from the University of Michigan, Ross School of Business where he was recognized as Entrepreneur of the Year.

I am a(n): Entrepreneur
Companies I've founded or co-founded: Stessa,, S3 Props
Companies I work or worked for: Edmodo, Amazon Web Services, Intel
Company exits (of companies you founded):
Achievements (products built, personal awards won):

Stessa gives the millions of real estate investors with single-family rentals and multifamily buildings a powerful new way to track, manage, and communicate the performance of their real estate assets. Property owners can now see all their key metrics in one place with a visual dashboard, automate their income and expense tracking, and save time with tax-ready financial reports.

If you are an entrepreneur, why? 
I love building products and solving hard problems.
My favorite startups: Wyze, Peerstreet
What's most frustrating and rewarding about entrepreneurship/innovation?

Most frustrating: The extreme highs and the lows of the day-to-day...although the rollercoaster is also what makes it all so invigorating.

Most rewarding: achieving product / market fit and getting lots of customer love.

What's the No. 1 mistake entrepreneurs make?

Lack of focus - trying to do too much.

What are the top three lessons you've learned as an entrepreneur?

1. Value your time appropriately. 
2. Surround yourself with great talent. 
3. Set regular, clear and measurable goals.

What inspired you to start Stessa?

My co-founder Jonah Schwartz and I didn’t start off knowing we would be doing a real estate technology company. Rather we started off contemplating a number of big ideas around the future of work,... yet we kept on getting distracted by our real estate portfolio. To get some immediate gratification, we did a deep dive into one of our multifamily properties that had been on autopilot for a couple years and ended up nearly doubling the value of the building.

We were shocked by how much value we were able to create in such a short amount of time and came away with three big takeaways:

1) As real estate investors, we should be applying these learnings to our entire portfolio.​ 
2) As product people, we could build software to automate nearly everything we just did. 
3) As entrepreneurs, there was a huge opportunity in the space to build a company around a technology solution that we could make available to the millions of investors like us who today use little more than a spreadsheet to manage their portfolios.

What is the origin of the name Stessa?

Stessa is 'assets' backwards.

Early on, we also had this concept of a real estate chatbot that could provide real-time insights about investment properties. ‘Stessa’ sounded like a nice person with whom I might enjoy discussing my properties. Who knows, we may have that chatbot in the future...

Bonus: Trust your instincts.

Related companies, investors and entrepreneurs

Description: Stessa is the essential tool for the millions of real estate investors with single-family rentals and multifamily buildings. Stessa offer...
Bio: A seasoned technology executive and entrepreneur, Heath is Stessa’s co-founder and Chief Executive Officer.

Related news


Featured Stories


Other episodes of this series

Today's Entrepreneur: Nir Leibovich


Today's Entrepreneur

by Abhay Vij
Always seek to learn and grow

Today's Entrepreneur: Esther Dyson


Today's Entrepreneur

by Kristin Karaoglu
It's amazing to be part of a team that works together and does so much more than any individual does

Today's Entrepreneur: Joe Du Bey


Today's Entrepreneur

by Kristin Karaoglu
The early team defines the later team; be selective and consistent across values and talent

Today's Entrepreneur: Matthew Kropp


Today's Entrepreneur

by Kristin Karaoglu
Making progress requires relentless pushing while also realizing that progress takes time

Today's Entrepreneur: Emi Gal


Today's Entrepreneur

by Steven Loeb
The quality of the startup is directly proportional with the quality of the team