Business Startup Spotlight: TSOLife


TSOLife was created with the conviction that life should be celebrated, passed down, and remembered. TSOLife seeks to be a home for personal stories, helping people to preserve their legacies and pass down life stories before it is too late.


Founder & CEO, David Sawyer

Name: TSOLife

Location: Tampa, Florida


Product / Service Offering: Online Platform for Documenting Life Stories

Co-founder Interviewed: David Sawyer, Founder & CEO

Other Key Management Team Members: Stella Parris, Co-Founder & CEO; Diana Dupre, CMO

This article is part of our Business Startup Spotlight series featuring entrepreneurs and their companies. We hope that these founders’ interviews will inspire and motivate you as you undertake your own entrepreneurial journey.

Tell us a little about yourself with a focus on what motivates you.

I have been a high-level athlete all my life, so I am motivated by winning. My competitive mentality drives me to build TSOLife to success. This desire gets me up every morning.

When did you establish your company and where did the idea originate?

The idea for TSOLife originated shortly after the passing of my grandmother. She had been one of the most important people in my life. Sitting at her memorial service, I found myself feeling like I never knew who she really was, and even more, that I would soon forget. My grandmother’s fingerprint on the world would never be deeper than her name, birthdate, and occupation. What was her personality like? What were her values? I wanted to know how she met my grandfather and stories from her youth. All of this ultimately magnified her loss for me.

TSOLifeA year later, in 2014, I founded TSOLife (The Story Of Life) so that one day, no one would have to wonder what their grandparents were like and experience the loss that I felt. As it currently stands, history is only recorded for the famous or infamous. The rest of us are left to be forgotten. TSOLife was created with the conviction that we are all worth remembering. Therefor, life should be celebrated, passed down, and remembered.

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What need or needs does your company seek to fill for its customers?

The comment we receive most is, “I wish I could have done this for my grandmother/grandfather.” TSOLife seeks to be a home for personal stories, helping people to preserve their legacies and pass down life stories before it is too late. We are providing the tools to document memories, turn them into stories, and share them with loved ones. Ultimately, it connects users with their decedents, and the magnitude of overcoming that challenge is powerful.

What is the one thing that sets your company apart from its competitors?

TSOLifeEveryone is attracted to the concept of TSOLife, but the challenge comes in getting people to actually sit down and document their stories. We have overcome this by making the life-writing process simple and enjoyable. TSOLife’s interactivity and simplicity distinguishes it from the competition. It is the first storytelling platform to use a step-by-step video guide led by a writing expert and coach. The user feels like they are filling out a template. Down the road, the company will have genealogy thought leaders and other popular memoir writers lead guest instructional videos.

What was the biggest challenge you faced while getting your company up and running, and how did you overcome it?

The biggest challenge I faced was trying to be a full-time college student and run a company at the same time. It is tremendously difficult to establish business relationships and channel partnerships, secure funding, offer high-quality customer support, manage employees, and succeed at every other component required of a startup while still in college. I dropped out of school. There is no part-time entrepreneur.

What resources have you utilized that other founders might find compelling or useful?

Y Combinator has been a tremendous resource. We are also working with Tampa Bay WaVE. Additionally, early on I watched a series of twenty videos by Sam Altman. This helped give me a grasp on what I should be doing. I highly recommend those.

What steps have you taken to secure funding for your company and what, if anything, would you do differently if you had to start over?

We have secured investments from several local angels who have ties to venture funds and are working with these small investments to reach milestones to assist in justifying a Series A. We started the company with $60K, but in retrospect, we should have multiplied that number by 1000%. It is very difficult to gain traction and meet milestones bootstrapping.

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What questions have you had as an entrepreneur of a fledgling startup that you had a particularly hard time finding the answers to?

The Silicon Valley ecosystem generates tremendous resources for entrepreneurs. However, growing a company outside of that area, say, in Florida, is difficult, and finding advice for that region is challenging. For instance, an angel investor in Boston or New York would call a Series A $2 million, while an investor in Florida would call it $400K.

When trying to figure out best practices and navigate the challenges of growing a startup, it is difficult to follow non-regional advice.

What challenges, if any, are you grappling with?

It is a challenge to find good employees. We are scaling at a rate of five times a year in terms of hires and doing so while maintaining the same quality of work and team dynamic is challenging.

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What is the most helpful tip or “hack” you’ve ever learned, stumbled across, or been given?

Innovation complacency is the death of all startups. You need to constantly be hungry and looking for growth. This piece of advice propels me to put everything into this company. Taking a comfortable salary and working 20 hours a week does not satisfy me.

Is there anything else you would like to share about your company?

Looking back, the biggest deal we have achieved to date occurred during a time of desperation. I sent an email to a “support” address. Try everything until you find what works.

Are you familiar with other startups you believe should be spotlighted? If so, we would like to hear from you. Tell us about them in the comments below!

Sandra Sloan

Sandra has previous supply chain and business operations experience which she is leveraging as an author with FundingSage focused on spotlighting entrepreneurs and their startup efforts.