Jennifer Simchowitz of Keepster: “Nothing is more important than believing in your product”

Nothing is more important than believing in your product. That’s what started me off and that’s what keeps me going. As you go forward your idea may well shift or change, but no matter what, it’s that fervent commitment to creating something new, or an idea for an improved version or way of execution, that […]

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Nothing is more important than believing in your product. That’s what started me off and that’s what keeps me going. As you go forward your idea may well shift or change, but no matter what, it’s that fervent commitment to creating something new, or an idea for an improved version or way of execution, that will help you survive the 3 am demons — and the 24/7 marathon way of life. The words passion and authenticity get thrown around a lot these days, but the truth is that is what it takes.


As a part of our series about “Why We Need More Women Founders”, I had the pleasure of interviewing Jennifer Simchowitz.

Jennifer Simchowitz had an idea for a Valentine’s gift for her significant other: a year’s worth of their text messages as they were falling in love turned into a book. After Googling around endlessly for easy tools to create the book, Jennifer discovered that they simply did not exist. The Valentine’s Day present that she had in mind was going to have to be laboriously handmade. Six months later, a beloved childhood friend of Jen’s passed away tragically and suddenly. Part of Jen’s healing process was going through their texts — whether daily check-ins, or planning who would cook what for their shared Thanksgivings. These were the moments that ultimately launched Keepster: a desktop app to save, search and organize text messages, and print the special ones into books.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

Mine is not one bit a traditional career story. Never in my life did I ever imagine becoming a Founder or CEO of a startup. Up until this chapter I’d been involved with the arts, with museums, had a one-of-a-kind jewelry design business and, most important of all was a mom. So there was nothing to predict that I’d be in the business of developing technology to preserve messaging conversations. But, looking back I can see that my education in art history (and being an archivist at heart) is the thread that led me here. In my case, events in my life also played a huge role. I fell in love, and for Valentine’s Day wanted to gift my guy a special gift — a book of our text messages — but discovered there was no easy way to do that. Shortly afterward my dearest lifelong friend passed away very suddenly. We’d texted almost daily through the years. Suddenly those conversations were silenced. A short time later I was at an exhibition of the letters of Hemingway. & F. Scott Fitzgerald. People were crammed in trying to read them. It struck me how in years to come there would be no such letters, given the ephemeral nature of our digital communications these days. So, these experiences of life, love, and loss made me search for a way to make these key messages of our lives permanent. And that’s how I landed up here.

Can you share the most interesting story that happened to you since you began leading your company?

As someone with no background in technology at all, every moment of building this company has been wildly interesting to me. But the most memorable and arresting stories have resulted from the one-on-one conversations that I’ve had with our customers. Each story about what led a customer to Keepster is something that I try to remember and carry with me in making choices how to make Keepster better .

I’ve spoken with families who’ve lost loved ones. One woman told me when she read over her book of the texts she’d exchanged with her late brother, “it felt like he was sitting next to her again, sharing jokes and swapping stories”. Just the other day I spoke with someone who during their actual wedding ceremony, presented his new wife with SIX books of their texting messages from their first date onward. So, as much as I have loved learning about the technology and business of building Keepster, in the end, it is always the human stories such as these that have impacted me the most.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I will never forget the final presentation I made when I was participating in a start-up incubator. At that time I was a total beginner, so there was nothing funny about having to present to an audience of many hundreds. I was so nervous I couldn’t stop shaking, my voice came out sounding super weird, sort of like I was being strangled. Simply put, I bombed. Looking back at it now it really cracks me up, but the biggest mistake that I made was that at the very last minute I decided to pivot my pitch to something that I thought the judges would want to hear, something that I thought would make the product seem to appeal to a bigger and broader audience. Wrong! The lesson learned? Speak your truth, talk about your vision, no matter how much you fear others may judge it.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

A friend introduced me to a wonderful, smart young woman with an MBA and a tremendous amount of experience in startups. She’s swooped in to help me out on a few occasions — helping me crunch numbers, figure out monetization opportunities, etc. But the way in which she has helped me the most is the encouragement she has continuously given me. I cannot count how many times she’s said, “ Plenty people have great ideas — but they simply remain ideas. You had an idea, you built it, and you launched it. “ The best part is that each time I get together with her, she says the same thing — and adds to it. The last time we spoke it was, “Judging by the rave reviews you’re getting you’ve reached product-market fit.” I can’t wait to hear what she has to say next time around!

Ok, thank you for that. Let’s now jump to the primary focus of our interview. According to this EY report, only about 20 percent of funded companies have women founders. This reflects great historical progress, but it also shows that more work still has to be done to empower women to create companies. In your opinion and experience what is currently holding back women from founding companies?

Personally, I don’t like to dwell on what holds anyone back. Rather I prefer to concentrate on what’s keeping the wind in one’s sails. Still, I must confess that as a woman, and a woman of a certain age, both of those factors at times, have seemed to count against me. Very often the feedback that I received was that my idea for Keepster was (cringe) sappy and sentimental — in other words too girlie. Ultimately, I think that what holds women back is what holds everyone back, and that is fear. But as a woman, you often need an extra dose of guts and belief in yourself to just keep going.

Can you help articulate a few things that can be done as individuals, as a society, or by the government, to help overcome those obstacles?

It seems that these days in the startup world there is an increasing number of communities and sisterhood-type organizations aiming to support women, by sharing their stories and providing networking opportunities. However, I have a vision for something larger. There should be many more organizations providing women with one-on-one mentorship, offering business, technical and yes, ‘psychological’ support. So often have I’ve wished for a good business ‘shrink’. Someone to talk me off the ledge, allow me to vent, or just be there for me to help confront my deepest darkest fears. Most of the time, particularly in the workplace, we women are obliged to act strong and fearless — and of course, we can do that well. But for me, the ideal would be to embrace women who’ve retired or exited the workforce. Sharing their collective expertise and life experience would be invaluable to rising generations. To me, it would be a very exciting prospect to bring together women who are in different phases of their lives, but who have in common the knowledge and will to take on the uphill struggle of building startups.

In past generations, we learned from our mothers and grandmothers. Clearly that’s no longer the norm. So, as a great believer in community building, this would be a wonderful way to share know-how, keep older generations feeling engaged and relevant, plus mitigate against the increase in fragmentation of communities and feelings of isolation in our societies. The organizations I’m imagining would be a contemporary re-iteration of women helping women, cross-generational knowledge sharing, and effective reciprocal support.

On a different note, there needs to be a lot more opportunities for retraining women, and as always more affordable childcare solutions.

This might be intuitive to you as a woman founder, but I think it will be helpful to spell this out. Can you share a few reasons why more women should become founders?

This seems like an odd question. There should be more women founders as much as there should be more women doing all sorts of jobs, presidents included! Still, I’m pretty certain that a product like Keepster would never have been dreamed of by the stereotypical tech guy. Keepster’s focus on memory-keeping, and on personal, intimate relationships, certainly feels anti male-tech culture. So there are lots of people out there, who are underserved by the current tech culture and who’d benefit from more women bringing their ideas to fruition.

There is also something about women that makes them really good at community building, plus they’re imbued with the “it takes a village” sensibility which means they tend to be great at working collaboratively. Also, women tend to be excellent multitaskers. I am not a fan of generalizations, but in this regard, I would say these skills are shared by most women that I know — and all of these qualities are key to building thriving startups.

What are the “myths” that you would like to dispel about being a founder? Can you explain what you mean?

The biggest myth is that a startup just takes off, like a snap of the fingers. Absolutely not true. In fact, the very opposite. It takes a lot of mistakes, false assumptions and time to do all the work in order for the data to tell all. There are no shortcuts to success.

Is everyone cut out to be a founder? In your opinion, which specific traits increase the likelihood that a person will be a successful founder and what type of person should perhaps seek a “regular job” as an employee? Can you explain what you mean?

I think everybody has the potential to be a founder provided that you‘re prepared to assume the risk of failure. At a 9–5 job if you do good work you will be rewarded. As a startup founder not only is the likelihood of failure very high, but if you have a chance at succeeding the odds are it will be quite some time till you are able to reap any of the rewards. If you want to be a founder you also need to be flexible, As a founder there is no such thing as a 9–5 day, and with so much work most likely to be happening remotely, across several time zones, you will need to be extremely flexible. To be a founder also means wearing many hats at once, particularly in the beginning when no job can be considered too small.

Ok super. Here is the main question of our interview. Based on your opinion and experience, what are the “Five Things You Need To Thrive and Succeed as a Woman Founder?” (Please share a story or example for each.)

I’m a little thrown by this question where it seems the slant is on gender. Let me answer this more as a person than as a woman.

1. Nothing is more important than believing in your product. That’s what started me off and that’s what keeps me going. As you go forward your idea may well shift or change, but no matter what, it’s that fervent commitment to creating something new, or an idea for an improved version or way of execution, that will help you survive the 3 am demons — and the 24/7 marathon way of life. The words passion and authenticity get thrown around a lot these days, but the truth is that is what it takes.

2. Being a founder requires clarity. Being a founder means facing a constant barrage of challenges that keep coming at you from every direction. The goal is to remain laser-focused, at the same time that there’s a multitude of tasks constantly yapping at your heels. In order to navigate all of this it’s essential to discipline oneself to regularly step aside to quieten the noise, gain perspective, and only then can you prioritize. One of the most helpful lessons I learned was from reading Bob Iger’s book where he says you can’t have more than three priorities. Anything more than that and it’s not a priority.

3. Being a founder takes a lot of patience. As an extremely impatient person, this is probably the most difficult lesson I’ve had to learn. I had an idea that it would take a while to get my product built and the marketing dialed in, but in reality I had no idea how much time it really takes. When I came across a picture of Jeff Bezos, sitting at his desk in a dingy warehouse office at least 20 years ago, it made me realize that that’s what patience looks like Also, I am frequently reminded of the LAUNCH Incubator’s Jason Calacanis words, when I was there: a startup is built by adding bits of kindling, very gradually, one at a time. In fact he said that if a startup takes off immediately, chances are that it will burn, crash and die. Regardless of these reminders I’ve committed the mistake that any founder will most likely make — rushing to build too many features to be all things to more people, all at once. Not only is it foolish, it turns out to be dangerously costly.

So here’s the simple rule:

Time + Data + PATIENCE = Smart decisions + a better shot at longevity

4. As much as it’s crucial to constantly stay laser-focused, a key ingredient is to learn how to pace oneself. I make time to cast the net wide for fresh ideas and inspiration rather than remain myopically bogged down in the minutiae. I scour the news for stories, for ideas, or for any buzz in our collective conversations, ranging from politics to culture to psychology, and beyond. Though we’re a technology company our business is about memory keeping, commemorating important relationships and human connection — in short, it’s about humanity. So in order to gain fresh inspiration, enlarge and refine our vision, I have to make time to plug into the world. Reading stories about how Amy Schumer proposed to her husband via text, or how a ‘badass’ group of women in Congress bond and banter about policy via text, or about a daughter’s heartbreaking last texting conversations with her mom during Covid are the kind of stories that fuel my conviction to give Keepster my all.

5. Courage is what has enabled me to survive and thrive, particularly as a woman. For most of my life I’ve walked my own path, whether choosing to do so consciously or not. But when it came to stepping into this entirely new domain — of technology and startups -, that’s where consciously choosing to cultivate courage has made the difference. I remember when I first moved to LA and the 5 lane freeways terrified me. But when I actually looked at the people, just sitting there in their cars and driving, I said to myself that’s not rocket science — I can do this — and over time that’s what pushed me from the slow lane into the fast lane. Years later, I often find I am giving myself the same kind of talk. “Take it one step at a time Jennifer — you can do it. Little steps, little steps.” That’s what builds courage.

But finally, the truth is no matter how much courage you have, you cannot do it alone. I’ve been blessed being surrounded by my team, who also have been my best teachers and who miracles of miracles have cared as much as I do.

How have you used your success to make the world a better place?

Our books exist to celebrate, commemorate and honor some of our most important relationships. So I believe that when our customers leaf through their Keepster books and revisit their own stories, the joy, laughter, or comfort that they feel really helps makes life sweeter.

Also, these days there is a much bigger discussion around the vast digital legacy that each person creates, how to manage it and how to preserve what matters. What Keepster does is provide a very simple solution to this enormous challenge. Whether you use Keepster to create books or organize and save\messages digitally, Keepster allows people to preserve their stories and make them permanent.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

Based on my constant preoccupation with human connection, I am deeply aware and concerned about the epidemic of loneliness that is so pervasive across all demographics. In spite of all the current research, and growing awareness around mental health, there doesn’t yet seem to be any clear systematic, community-based solutions to this problem. Still, I am continuing to learn whatever I can about this issue, and my goal is to come up with some more concrete ideas soon.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

That question must have a one-word answer from so many people — and that word is Oprah!

Oprah is the queen of exploring our most human stories. Keepster books are also about giving people a way to tell and share their stories. I cannot think of any better person to talk with about this very unique and personal kind of storytelling!

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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