How to Build a Tech Company, Raise a Family & Harness AI with Shira Simmonds

You're listening to the Jewish Entrepreneur Podcast with Debbie Sassen, episode No. 178. Welcome to the Jewish Entrepreneur Podcast. I'm your host, Debbie Sassen. I went from being a financial advisor, author, and chronic under-earner to building my business to six figures as a financial planner and money mindset coach, and then onto multiple six figures as a full-time money and business coach. I help entrepreneurs create money-making businesses and build wealth using sales and money mindset strategies and in alignment with authentic Jewish values.

Now let's dive in to today's show.

Hello, my friends, and welcome back to the podcast. I'm recording this introduction for you from the Grand Tetons. I am here in the mountains with my husband—we're on a little holiday. It's been quite a year, or even like 21 months in Israel with the war that's happened with Gaza and then Iran since October 7th, 2023. We took some time out to be together, just the two of us. We're in the mountains, surrounded by fresh air and wild animals. Yesterday we were on a river cruise, on a raft, and we saw many bald eagles, osprey, and it's just been a time for us to unwind, relax, and enjoy the stillness of life—not the hustle and bustle, not the AI that we're going to be speaking about today in this interview with Shira Simmonds—but just time for us to slow down and be together and reconnect with nature, reconnect with each other.

While it seems that what I'm doing right now on holiday with my husband is the polar opposite of artificial intelligence, I think the balance that we have—the work-life balance, or work-life harmony as I like to say—is really where you have that sort of secret sauce. There's the innovation part, the systemization of your business, and increasing the efficiency and productivity. That's what's going to sustain your profitability as a business. But in order to do that over and over again and really have that clear head to focus and grow your business, become more profitable, and focus on your clients, your audience, your people and what they need, you also need a pause. You need stillness. You need time to unwind. And that's what I'm doing—except for this little tiny intro that I'm bringing to you, that I'm recording from the Grand Tetons.

Let me just give you a little bit of background and then we're going to jump into this interview, which is fantastic. Let me just introduce you to Shira Simmonds. She is a powerhouse—she's a tech entrepreneur and she's built not just one successful business, she's built two successful companies. She's the CEO of SSS Digital and the founder of Smart Reach AI, where she uses data and automation to drive sales and scale growth without losing the human touch of her business.

In this episode, Shira and I are going to speak about the real journey of building a business. We're going to talk about success, failure, pivots. We're going to talk about being a mom and growing a business. Shira is a mom of four children and she's been able to grow her business through pregnancies and leadership and family, moving to Israel—all the things. We're also going to speak specifically about how you, as the owner of your business, can use AI—artificial intelligence—to free up your time so you can spend more time with your family. So you have more time instead of being in the weeds of your business, to grow your business profitably. And you're going to know by the end of this podcast what it really means to scale your business without burning out, without becoming a robot or your business a robot. Because we are here as people, working with people, serving people.

You're going to know what that means for you and your business. So let's dive in…

Sure, I am so happy to have you on the podcast—welcome. I know we're going to have a great conversation today.

"Thank you, Debbie, so happy to be here. I think it's crazy that you and I live probably a stone's throw from each other in Israel, and we've never met. We just connected today, like an hour ago on LinkedIn, where you spend a lot of time and I spend a lot of time. So this is going to be a great conversation—just letting our audience know how people find you, connect with each other.

And what I really want to do is start with your story. Because, you know, we've talked a little bit about your story of resilience. I know that your business has taken a few iterations until you started doing what you're doing. So start wherever you feel is comfortable. I know you've been in Israel about 14 years, but what did you study in school, and how did you end up where you are today?"

"Okay, so I went to the Sy Syms School of Business, aka 'earn college for knowledge.' I majored in Management Information Systems—I think it was one of the first years that they actually had that major. I always knew that I wanted to go to business school. I was born and raised in Toronto and always knew that I kind of wanted to move away from Canada and get to Israel. I thought that being in a Jewish university would be the best step for me."

"I really wanted to be in business. I loved marketing and entrepreneurship, but there was no major in entrepreneurship at the time. This was around 1996 or 1997. We were just learning how to use computers. I remember going to the computer lab to sign into our AOL email—just to date me!"

"Wait a second, can I stop you here? I'm a few years older than you. I was a freshman in college in 1981, and I took a computer programming course in Pascal. I thought I would love it, but I never progressed. I worked in the computer lab, though—there was no email at that time, and I worked the graveyard shift because it was great money. We had dot matrix printers, and I helped people unjam their printers. Computer labs have been around a long time!"

"Funny though—I have to say, my bat mitzvah was like the beginning of my entrepreneurial spirit. My father, who has had his own company for over 40 years, got very early into computers—buying and selling computer systems and servers. At my bat mitzvah, he brought huge computers and set it up so guests could type in their names to find their table numbers. It was revolutionary at the time."

"Most people didn’t even know how to type yet. It was hilarious watching them try to find the keys."

"Wait—what year was your bat mitzvah?"

"I was born in 1976, so sometime in the 80s."

"I grew up in Los Angeles and worked in my cousin's electronics shop over Christmas and summers in the 70s. We were selling the first Macs, Apple IIs, 486s, Commodores, and Texas Instruments. Those early computers were something else."

"Yeah! I didn’t go into programming, but I always loved business. I had a lemonade stand at eight, and I’ve been a businesswoman forever."

"Me too! Growing up in Toronto, I was a competitive gymnast from age 3 to 16 and also religious, which made competing difficult. I couldn’t wear a leotard in front of men anymore, so I stopped and became a telemarketer at 16. I still remember my sales script—people would scream at me for saying we had surveyed their property, but I was the top seller!"

"Even before that, in Grade 8 (we say 'Grade 8' in Toronto!), our class didn’t have enough money for our graduation trip. So I contacted wholesalers and sold flowers and knick-knacks every week for Shabbos. We raised enough money to go to Washington, DC!"

"I didn’t need to make money—we lived comfortably—but I loved the feeling of making my own money. My bat mitzvah trip to New York included shopping at Bloomingdale’s. I saw a $99 dress I loved, but I told my mom not to spend that much on me. Even then, I calculated how many hours I'd have to work to afford it. That was a big moment in my money journey."

"In business school, I realized computers were the future. I hated programming—I cried through my classes—but I loved finance, accounting, and marketing. I struggled in high school but thrived in university. I couldn’t wait for my classes. I just wanted to build and solve problems."

"I got married in 1997. My husband was in a special program at the Technion, and we moved to Israel right after our wedding. He was in medical school, and I had been accepted to Bar-Ilan’s MBA program, but we didn’t have a car, and we were broke newlyweds. So I worked instead."

"My first job was awful, but I moved up to a great company where my boss became my mentor. He started a company and took me with him. Then we moved back to the US for my husband’s residency and fellowship. I had one child in Israel, two more in the States, and one more after starting my first company."

"And yeah, I have so many stories to share. Let me know specifically what you want to know. I have wild investor stories from my first company—this is actually my second company, and Smart Reach is a spin-off of it."

"What I want to talk about—because you were in the computer space—I don't know exactly what the company was when you were working in Israel, but we also had the dot-com bubble that burst in 1999–2000. How did that impact what you were doing at that time?"

"Interestingly enough, as a frum girl, I ended up working for a company that developed software for online casinos. My job was to buy media to get people to gamble, which I struggled with internally. I was really good at it, and it was this whole new world of being able to play blackjack, poker, or slot machines online. I was always more on the marketing and advertising side rather than programming, and I loved it. I fell into that role because I was one of the English speakers in the company."

"I was also the voice for antivirus software—I’d say 'virus alert' in the program. I was involved in all sorts of things."

"Wait—when you say 'buy media,' can you explain that?"

"Sure. Buying media means buying online ads—like Google ads today. At that time, we didn’t have Facebook yet. I'd buy space on publisher websites, game sites, news sites. I had a budget and allocated it where we'd get the best ROI. I even created a platform to track all of it and measure results."

"Wow. And you loved that part?"

"Yes, I loved the analytical side. Even though I struggled with math in high school, I thrived with it in university and especially when tied to business analytics. I loved understanding what was converting and why. But ultimately, I left that company. We’d get emails from people saying they gambled away their kid's college fund, and I couldn’t deal with that morally. I came home crying to my husband."

"One day, while pregnant with my fourth child, I was at Target and saw a woman digging into her diaper bag for a coupon. I thought—what if her coupon was on her phone? That was my lightbulb moment. Brands could communicate directly with people on their phones."

"This was pre-smartphone, just SMS. So I started my first company—Ping Mobile. I developed the concept and hired a programmer in India with maxed-out credit cards. The experience was awful, but I learned a lot."

"Eventually, I partnered with Cox Communications, a huge cable operator. My idea was to use text messaging during TV commercials. People could text a code and get a coupon, which allowed us to track engagement. It was revolutionary."

"When Cox wanted to visit my office, I didn’t have one—so I borrowed a friend’s office space and staged it with family photos and branded materials. We signed the deal there."

"That’s incredible—and bold!"

"Yes. I did whatever I had to do to make the business look legitimate and get deals. My husband was my biggest supporter. I had invested in him during his medical training, and he supported me now. But we were in a bad financial position. I eventually had to take money from a toxic investor and lost a lot of equity."

"Did your parents help?"

"Yes, my parents were my first investors. But building a tech company requires millions, and their support wasn’t enough. I felt tremendous guilt about losing their money. It was one of the biggest lessons of my life."

"And then, while eight months pregnant, I pitched to a fund in Boston. They didn’t know I was pregnant until I stood up to shake hands. They never signed. I later learned it was because of my pregnancy."

"Would you do it differently today?"

"Absolutely. I would be honest from the beginning. I let someone else’s advice override my gut. Today I trust myself more."

"When I started my second company—SSC—I promised myself I’d do things differently. After moving back to Israel, I realized I couldn’t run Ping Mobile anymore. It was an American company, and with four kids and making aliyah, it just wasn’t feasible. So I started consulting. That was my vision. I built SSC around that model."

"That was 13 years ago, right?"

"Yes. I decided I would consult solo, lean on my American relationships, and just help companies connect with partners or pitch to brands. But it grew quickly. I said I’d never build a team again, never raise money, but that changed. I started hiring people—first in the Philippines, then in Bangladesh, and later South Africa. SSC became a full agency, and at one point, I had over 100 people on my team."

"That’s incredible. How did you manage a team that size—especially as a mom?"

"I have a lot of energy. I’m an early riser and a late worker. But time zones were the hardest part. I couldn’t afford to hire in Israel, so I built a global team. I hired general managers in each country to manage their teams—Philippines, Bangladesh, and South Africa. I had 6 or 7 direct reports who ran operations. It worked."

"Then came SmartReach AI, right? Tell us about that."

"Right. I realized SSC wasn’t scalable. We were doing manual research—checking each prospect’s website, number of employees, job titles. Every new client meant hiring more staff. It was inefficient. I had been thinking about solving this problem for years."

"We had sent over 25 million cold emails through SSC. I knew we were sitting on a goldmine of data—what subject lines worked best, which audiences converted, optimal send times. But no human could analyze it all efficiently. That’s where AI came in."

"At first, I worked with some bad developers—one took $15,000 and didn’t deliver. Eventually, I found an amazing agency in Ukraine through Upwork. They helped build the architecture I needed. I reduced my team to 30 people and reinvested the savings into developing the platform."

"I also had to shut down our Bangladesh office due to political tensions—they were posting antisemitic content online. That was difficult. But we transitioned and automated much of the work."

"What does SmartReach AI do exactly now?"

"It started as an AI-powered tool to personalize outreach emails—using data like a prospect’s recent podcast or LinkedIn posts. But people caught on that it was AI-generated, and response rates dropped. So we pivoted."

"Now, users write the core email in their own voice and add personalization tags for AI to fill. We also added editing tools so the AI learns your tone. Plus, you can instruct it to avoid overused words like 'tapestry' or 'just circling back.' It’s now a true collaboration."

"And you also use AI for research?"

"Yes, that’s the big shift. Before you reach out to a lead, you can ask AI to research them—are they B2B or B2C, do they offer AI services, etc. It’s real-time, detailed, and efficient. That’s where SmartReach is now focused."

"I love that. It’s a great reminder that AI can do more than write—it can help us make better decisions."

"Exactly. It’s about knowing what tools exist and how to connect them. The future isn’t about replacing people—it’s about enhancing what we can do with less time and more intelligence."

"Thank you so much, Shira. This was incredible. I know our listeners will walk away with so much—from how to take risks, deal with setbacks, and use AI strategically without losing the human touch."

"Thank you, Debbie. It was an honor."

"All right everyone, we’ll include Shira’s links in the show notes so you can connect and learn more. See you next week on The Jewish Entrepreneur Podcast."

"Thanks for listening to The Jewish Entrepreneur Podcast. If you want to stop underselling and under-earning and close more sales, you need to clear the limiting money beliefs that are sabotaging your business growth. Head to debbiesassen.com/mindset to download my free money mindset workbook. Hundreds of entrepreneurs are now building six, multi-six, and seven-figure businesses by creating true financial freedom. Join them today."