The Day I Ventured Out – Sarabeth Jaffe, Co-Founder and CTO of HelloPrenup

July 1, 2021

1. What were you doing before you launched your startup?

I was working as a Software Engineer at Karat, a Seattle-based startup that conducts technical interview screens for rapidly growing engineering teams.

2. When did you realize you wanted to quit your job?

At the beginning of the COVID-19 pandemic I was stoked to work from home for 2 weeks. I’m an introverted Software Engineer– this will be awesome! I was really excited to work in my pajamas and spend more time with my rescue dog!

But, after 9 months of isolation from my colleagues, friends, and family… the excitement disappeared. Before resigning I actually took a couple weeks off for mental health. (I am incredibly thankful to have been part of such a supportive team!) I officially resigned in late October 2020 (before the election because that was another huge element of stress) and spent 2.5 months completely recharging, focusing on self development and learning.

3. What initial hesitations did you have about quitting your job and how did you overcome them?

– Financial stability: I made sure I had a good cushion of savings and knew my monthly burn rate. We also decreased our rent by moving outside of the city.

– Health insurance: I knew getting health insurance was crucial during a health pandemic. I ended up keeping my insurance through COBRA and later switched to a public market plan.

4. Can you remember the day you put in your notice? What was it like, what was going through your mind, how did your manager take it?

My manager was very supportive as was the rest of my team. (Karat is an awesome company to work for and are actively hiring for many roles.)

The day I gave notice I felt a huge sense of relief. I knew I would have time to just live and survive through the pandemic without daily job responsibilities. Entrepreneurship and starting my own company has always been my end goal, but I didn’t know how soon it would be coming my way!

5. What are you doing now?

I am now the CTO & Co-Founder of HelloPrenup, the first digital platform for couples to seamlessly create prenuptial agreements. 

HelloPrenup makes obtaining a prenuptial agreement affordable, fast, and easy! Everyone who gets married has a prenup, they may not know it yet. Those who do know it, realize how difficult and expensive it can be to draft a prenup. It shouldn’t be so hard! HelloPrenup is the first online platform to offer valid prenuptial agreements created using smart algorithms, offered at less than a third of the cost of a typical prenuptial agreement, and requiring a fraction of the time it takes to draft a prenup through attorneys. 

HelloPrenup charges a transparent, flat rate fee of $599 per couple for a prenuptial agreement, and the process takes about 2-3 hours from start to finish, whereas attorneys charge $2,500 per individual, on average, and the process takes 3 months!

Why a prenup in the first place? Through the use of prenuptial agreements, anyone can protect their financial interests and avoid potential economic pitfalls that can befall many married couples by controlling what happens to pre-marital property, business interests, change in income, among many other factors.

Use discount code VENTUREOUT for $100 off your prenup! (Expires 08/01/21).

6. Looking back on your experience of founding a company, what do you know that you wish you knew before? Are you happy with your decision?

I had never worked on a direct B2C product. Many Software Engineers think that if you build a good product, people will come flocking to it. But people can’t use your product if they don’t know it exists!

SEO and online marketing were completely black boxes to me. I have learned so much about the importance of content and online presence for building a consumer focused business.

7. Any other advice you can share for others contemplating a similar path?

Find a Co-Founder that is an expert in the industry you are looking to innovate in (especially if you are the technical Co-Founder!) 

In February 2021, I recognized the need for innovation in the prenup market– millennials are getting engaged and we demand modern solutions for everything we do! The traditional prenup process of vetting 2 divorce attorneys, paying uncapped hourly rates, and waiting months… all while planning a wedding… is the opposite of what we want! 

As a lone Software Engineer I knew I would either need: a Legal Co-Founder or a Legal Advisor to make my vision possible. While conducting competitor research, I came across HelloPrenup and reached out to Julia Rodgers, HelloPrenup’s CEO and head of Boston’s premier family law firm. (Advice: as an entrepreneur you really have to get over any fear of cold emails or phone calls!) It turned out that our visions to disrupt the prenup space aligned perfectly! With Julia’s legal and my technology expertise, we have grown the business exponentially since teaming up in March 2021.

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