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Raw and Real Entrepreneurship Podcast Interview with Susan Sly and Karen Gordon.In this Raw and Real Entrepreneurship episode, Susan Sly talks to Karen Gordon, co-founder of Simpli5. Karen shares her journey from managing a thriving business with $1 million in monthly revenue to navigating that customer’s bankruptcy. Her story highlights the importance of perseverance and strategic pivoting.

Karen shares the practical implications of cognitive diversity. She discusses the importance of understanding one’s strengths and actively seeking out and surrounding oneself with diverse individuals who possess complementary skills and perspectives. She explains this is the key to building high-performing teams that foster collaboration and innovation.

Karen and Susan discuss balancing work and family responsibilities, emphasizing the importance of setting boundaries to prevent burnout and the role of flexibility in fostering a supportive work environment. Karen shares her experience managing her company while dealing with her daughter and husband’s cancer diagnoses. They also address gender disparities in entrepreneurship, particularly women’s challenges in securing funding.

Tune in to be inspired by Karen’s resilience and gain actionable insights on leading with passion, embracing flexibility, and harnessing the power of diverse teams to drive high performance.

Topics Discussed In This Episode:

  • Entrepreneurship, resilience, and leadership.
  • Pivoting after a major customer goes bankrupt.
  • Gender disparities in entrepreneurship and investment, with a focus on women’s unique strengths and challenges.
  • Work-life balance and education for corporate success.
  • The practical implications of cognitive diversity and building high-performing teams.

About Karen Gordon:

Karen Gordon, Co-Founder, President, and CEO of Simpli5, is a visionary leader dedicated to transforming workplace cultures through collaboration and team performance. Recognized as a two-time Inc. 500 Honoree and Ernst & Young Entrepreneur of the Year finalist, Karen’s expertise is featured in top publications like The CEO Magazine and Huffington Post. Her TEDx talk on “The Myth of Difficult People” highlights her thought leadership in navigating complex workplace dynamics. Under her guidance, Simpli5 partners with Fortune 500 companies, universities, and healthcare organizations to promote cognitive diversity and productivity.

Connect with Karen Gordon:



About Susan:

Susan Sly is the maven behind Raw and Real Entrepreneurship. An award-winning AI entrepreneur and MIT Sloan alumna, Susan has carved out a niche at the forefront of the AI revolution, earning accolades as a top AI innovator in 2023 and a key figure in real-time AI advancements for 2024. With a storied career that blends rigorous academic insight with astute market strategies, Susan has emerged as a formidable founder, a discerning angel investor, a sought-after speaker, and a venerated voice in the business world. Her insights have graced platforms from CNN to CNBC and been quoted in leading publications like Forbes and MarketWatch. At the helm of the Raw and Real Entrepreneurship podcast, Susan delivers unvarnished wisdom and strategies, empowering aspiring entrepreneurs and seasoned business veterans alike to navigate the challenges of the entrepreneurial landscape with confidence. Dive deep into the essence of success with Susan Sly and redefine your entrepreneurial journey.

Connect With Susan


Listen to Susan’s Previous Interviews


Read Full Transcript

This transcript has been generated using AI technology. There may be minor errors or discrepancies in the text.

Susan Sly 00:00:

Susan Sly 00:00: Hey there, Susan here. I hope you are rocking your day. I acknowledge you for taking a few minutes to invest in yourself, your knowledge, and wisdom here on Raw and Real Entrepreneurship. There are a lot of changes coming up to the show, and I encourage you, after this episode, to go check out my latest startup diary, where I'm chronicling everything that's happening with the build of my new company, from the very beginning to what is going on now. My guest today is an incredible founder, and she has co-founded a company that is a piece of technology being utilized by Fortune 500 companies to help their CEOs discover their strengths, know where the best places to expend their energy are, and most importantly, to know themselves. When we think about why companies fail, it's often because the founder is putting their energy in too many places that don't make sense, or they don't have the right team, or the team doesn't have the right strengths. Today, we're going to unpack that. This particular founder is so resilient. You're going to hear about her journey during the recession, what it's like when your largest client goes bankrupt, and how she navigated that along with her family challenges. She stepped in as a wife, mom, and grandma when her family needed her the most, yet her company actually grew during that time, even though she was working less. She's going to tell you how she did that. She is the co-founder at Simpli5, a software utilized by Fortune 500 companies, leading universities, healthcare organizations, and more to boost team collaboration and success. Some of her clients include LinkedIn, VMware, and Sutter Health. This founder is the one and only Karen Gordon. As we go into the show, don't forget to hit the subscribe button. There have been some changes over at Apple, so a whole bunch of subscribers with the update are still not subscribed to the show. Make sure you do that. Wherever you're listening to the show, whether it's Spotify or anywhere else, hit the subscribe button so you don't miss an episode. And if you aren't following us on YouTube, go over to Raw and Real Entrepreneurship on YouTube because all of our episodes are there as well. With that, let's go ahead and you can hear my interview with the amazing Karen Gordon. This is Raw and Real Entrepreneurship, the show that brings the no-nonsense truth of what is required to start, grow, and scale your business. I am your host, Susan Sly. Hey everyone, wherever you are in the world, I hope you're having an amazing day. I was having such a good conversation with my guest today, like, "Oh, we got to record." We have so much in common. We're mothers of dragons. I mean, we're mothers of four children. We have some of our favorite states in common and just incredible journeys. I admire this woman so much. As I was sharing in the intro, she is a multi-time founder who has navigated incredible challenges. Karen, I'm just going to jump right in. I want to go to pre-recession. You were helping a company go from a million dollars a month to zero in a month. As the world was collapsing, you seemed to bounce back from that. I was in so much awe while researching and preparing for our show today. Could you share and tell everyone what the company was and walk us through what happened?

Karen Gordon 03:59:Yeah, well, first of all, thank you so much for having me on the show today. I really appreciate it, and I'm looking forward to our conversation. That was an interesting time right around 2008 when everything went south. It had been a great ride, and we grew very, very quickly, 1,100% in three years. My biggest customer went bankrupt. At the time, they were doing about a million a month with us, like you said, and they went from a million to nothing overnight. I had to say, "Okay, what's next? How am I going to pivot?" I've been entrepreneurial my whole life and decided it was time to build something new. Luckily, I came across something that I was very passionate about because I can tell you, with that first company, we had tremendous growth, tremendous external success, but I was pretty miserable because I didn't love what we were doing. We were doing telecommunications, data training, documentation, and RF engineering, but it wasn't changing the world. It wasn't changing people's lives. I found myself doing a ton of volunteer work to try to fill that satisfaction part of life. With this company that I have today, I'm able to have both success and satisfaction. It blends that giving-back ideal that I have as well as being able to do something entrepreneurial, which I've always loved.

Susan Sly 05:27:
You mentioned something really key about this sense of fulfillment, right? Especially as women, when we look at the data on women-founded companies, women are resilient. We often stick things out for long periods of time. One of my friends, the founder of Union Femme Wines, during the recession, lost her champagne bar in New York. Just disclosure, because I have to FTC disclose, I'm an investor Une Femme Wines. I had Jen on the show. She took what she had, Karen, and those resources, and she went on to found this company. Now they're doing business with Delta, Neiman Marcus, and they were just in Times Square. It's incredible. My question for you is, you're going through this, and there had to be this moment. I'm not a roller coaster person. My daughter, Avery, loves roller coasters. She and my husband will go on, but you know the ones where they just drop you like crazy. There had to be a moment when that customer went bankrupt that you had that leg moment. Can you talk about that? Because I know we have listeners right now who are maybe on the cusp of that. What was that like for you?

Karen Gordon 06:45:
Yeah, I think the hardest part of it was actually the people, having the people that work for me and depend on me. Fortunately, we were able to give them time to find other opportunities. We had enough in cash reserves that I was able to keep them on until they found their next opportunity. That was the hardest thing, just feeling like I was letting them down and that I didn't want them to have to suffer because this happened. Fortunately, we had planned appropriately and were able to do that for them.

Susan Sly 07:18:
How did you handle it emotionally? Because, you know, we're looking at this 16 years ago, right? The kids are teenagers.

Karen Gordon 07:29:
Yeah, I mean, like you said, I've always been pretty resilient, and I've had a lot of faith in my ability to do the next thing. My gift, if you look at my 5 Dynamics, is I'm high explore and high execute. So I see opportunities in the strangest places, and then I can create something from those opportunities because I have the energy to actually do something with those ideas. I was just able to lean on that and have that blind optimism that it was going to work out. Fortunately, it did. If you look at the statistics of women who create successful businesses over a million a year, it's a very, very small number. It's less than 2% of women-owned businesses that become over a million dollars in business. To be able to do that multiple times, it's just something that's in my DNA.

Susan Sly 08:25:
It is rarefied air. Those same statistics show that women-led startups are more profitable than male-led startups in the first two years. As a technology founder, why do you think that is?

Karen Gordon 08:49:
I think we have to be very careful with what we do have. It's so difficult to get funding. Honestly, throughout my whole career, I had enough opportunities that I never really felt the big difference between women and men until it came time to look for outside investment. That is the one space where I absolutely saw a difference. I was looking at some of the ideas that were being funded and thinking, "I would never put my money there." Here we are with a successful business growing quickly, and it was so tough to find people to invest in the business.

Susan Sly 09:23:
Yeah, I feel that women have to prove themselves more, and I know that firsthand. I always felt like you did. The analogy I gave was this: less than 2.5% of women-led pitches to VCs get funded. We saw a lift in that starting in 2023. We'll see what the 2024 numbers are. When you look at brown and black women, they make up 0.1% of that 2.5%. We're about 68% more profitable those first two years. I just got back from Silicon Valley and Canada. I'm an angel investor, and I also invest in the stock market. If I knew a stock was going to perform 68% better, it would be attractive. What in the world? It's ridiculous. The analogy I gave was, I grew up running track and field. It's like everyone's running the mile, but as a woman, I have to start a whole lap back. To your point, some of the things that get funded are really... I have a friend, he's a multi-time founder with many exits. He's like, "I've never even done a PowerPoint." Yet, I'm the person who is OCD about any of my decks that I'm putting out. I feel that women are scrutinized more. Do you think that's the case, that we have more to prove?

Karen Gordon 10:55:
Well, certainly what I've been told and I've seen in the data is that we're asked different questions when we do pitch, and they're very concerned about the data and about very minute things, whereas they buy into the person more with the man. Honestly, we've done studies with over 60,000 people who have completed our methodology or assessment, and we've looked for differences from a neural pathway perspective, from a brain perspective, and there really aren't. There are very slight differences between the way we think and the way that men think. So to me, if I'm an investor, I want to know, does the person I'm investing in understand their strengths, and are they surrounding themselves with people who complement those strengths? Because none of us have awareness in all of the dynamics required to make a business successful. Some of us are great on ideation, some are great on connecting, some are great on detailed work, and some are great on getting things done. We're a blend of those energies, but none of us are high in all four. So to me, a great leader is someone who surrounds themselves with other people who complement them.

Susan Sly 12:05:
And what do you think your superpower is, if you had to pick one?

Karen Gordon 12:10:
Definitely the strategy piece, the ideation piece, seeing things that others don't see, being able to see two and three steps down the line. Oftentimes with customers, if we're talking with a customer, I'll say, "Okay, if we say this, then this is going to happen. If we do this, then this is going to happen." So it's being able to predict the future, if you will, and just seeing what's on the edges. That has always been my superpower.

Susan Sly 12:34:
Well, that's it. I'll have to ask you in a moment what you are seeing for the future. We'll talk about that. Going back to you, you decided to acquire a company. I pause here, girlfriend, for a minute because, okay, your biggest customer goes bankrupt. Fortunately, you have cash reserves. From what I've researched on you, you're very fiscally conservative, brilliant. So you're able to support your employees. Some people would be like, "I'm just going to take some time off or get a job." No, you go right away and buy a company. Talk about that.

Karen Gordon 13:15:
I bought the intellectual property because the company itself, the gentleman who was running it, he was a brilliant scientist, learning diagnostician, and social psychologist, but he was not a businessman. I didn't want to inherit the issues that he might have created. So I bought the IP and created a new company. I'm always thinking that way. As a matter of fact, I know what my semi-retirement plan is going to be. I bought 18 acres in Maine on a lake, and I know I want to host leadership retreats there. That way, I can work part of the year and not the whole year when I'm ready to get to that point.

Susan Sly 13:50:
Invite me, I'm coming! Since you and I both have great memories there, we'll make some epic Maine blueberry pancakes, sister, and it's going to work. It'll be amazing. That was one of the things Karen and I were talking about before the show, our mutual love of Maine. It's like God's country. So yeah, semi-retirement. I can't even, in my 50s, I just laugh. I don't even say the R word because it's not happening. I come from a long line of people who don't retire, they just expire. So that is my retirement plan: death.

Karen Gordon 14:31:
Yeah, well, we say rewire instead of retire, basically. So it's just shifting what your focus is, but no, I certainly don't see myself just kicking back and doing nothing anytime soon.

Susan Sly 14:41:
No, and I have the longest list of things I want to do in life. As a sidebar in my research, Karen's mother decided at eight, if I have this right, that she wanted to go to Turkey, and she started learning Turkish. In my former past life, when I was co-founder of Radius AI, we had an office in Turkey. That's not an easy language. Oh my gosh. You clearly have it in your DNA. There's a whole long road ahead of you with so many things to accomplish. I want to ask you a question. You bought the IP for this company and spun up a new company, really taking a look at what makes humans tick, how they make decisions, and how they grow into their leadership. What was something perhaps surprising you learned from that data?

Karen Gordon 15:49:
For me, the reason I was attracted to this methodology is because I had been such a young leader with my first companies, and I didn't know anything about how to lead. It was a blind spot. As I mentioned to you before the call, I'm lowest in what we call Excite, which is being focused on people and looking at what their needs are. I had tried other things in my previous companies, brought in other products, and thought, "Okay, that's interesting," but it didn't really change my life. It didn't change the way that I lead, and it didn't give me immediate actionable insights. When I was introduced to this methodology, that's what happened. I was a customer first who fell in love with the IP and knew that Mike didn't care about corporate America; that was never his focus. He was focused on education, helping students get unstuck. I saw the opportunity to utilize this with getting teams and leadership teams unstuck, in particular, but just anyone by understanding what they do naturally and what they miss. For me, that's really why I was so attracted to it because it helped me as a user first.

Susan Sly 17:02:
That is so often going back to my husband, Chris, and I were talking about just in terms of strategy and thinking about Warren Buffett: don't invest in something you don't understand. I would add, don't invest in something you're not highly curious about because curiosity is what solves problems. Like Edison, right? If he wasn't curious about solving that problem, he would have given up after 1,000 tries, not, I think, 2,000, to get the light bulb. Even with what I'm building at The Pause, being a woman in menopause, I get the problem, and it's very easy for me to understand it. I have a curiosity around it, which I know you do. One of the things I read is what happened around 2018. Your daughter gets diagnosed with cancer, then your husband gets diagnosed with cancer. There are a lot of discussions on entrepreneurship, and I know you've been interviewed many times, as have I. It doesn't always get to the gaps and realness of building a company. We're focused on the event, but what about our personal lives and what's going on behind the scenes? I would say, and I haven't seen the data, but women are able to have challenges happening and still produce because we are wired that way, whereas sometimes it takes people out of the game. Let's go back to that moment. Your baby girl is diagnosed with cancer.

Karen Gordon 19:04:
Yeah, it was a crazy time. We had spent a couple of years trying to come up with a new product, a new platform. It was released in 2018 as well. Both my daughter and my husband worked in the company. So not only was there the personal aspect, but there was the company void as well, and everybody needed to lean in. With Emily, it was shocking because she found out because she took a fall at a CrossFit competition. She was a healthy eater, worked out all the time. She had a tumor that was 18 centimeters, and when she took the fall, it dislodged the tumor, which started creating pain. She went to the doctor thinking she'd broken her tailbone or something, and they found this tumor. The type of cancer was one that's never even had one study done on it because they've never had 50 people who had it that they could research. It was absolutely terrible, trying to have your 30-year-old daughter being diagnosed. Then, like you said, four months later, my husband was diagnosed with cancer as well. It was just one of those things that you do what you have to do. What I had to do was keep the business going. I would spend a week with Emily while she was going through her chemo treatments, and then I would stay to take care of her two small children because she was a single mother. Then I would come back, and my husband would have chemo, and I would be with him while still working in both places. Then I'd have a week off, and it would start all over again. This went on for six months.

Susan Sly 20:34:
So your superpower is curiosity. I have 10 questions but will limit it to a couple. Going back to Emily and the kids, how did you navigate your day? How old were her children at that time?

Karen Gordon 20:54:
Five and twelve.

Susan Sly 20:57:
As a mom myself, five and twelve, there's the school run, and five is busy, busy, maybe different bedtimes. Twelve is like, needs different things, the teenage years. How did you navigate leading your company and essentially stepping in as a mom and being there for your daughter? How did you structure your day? Did you reduce the amount of time? Did you set boundaries? How did you do that?

Karen Gordon 21:28:
Yeah, you know, it's really the same way that all of our employees work, which is with total flexibility. And so what that means is we set goals, we align on goals every single quarter, people know what they're supposed to do. And then it doesn't matter what time of day they do those things. It's just about you just get it done when you can get it done. And so, of course, yes, we take the kids to school. Emily, bless her heart, during that chemo time, she slept a lot that first week. And so really there wasn't a whole lot that needed to be done. So after the kids were at school, then I was able to get some work done. And then, of course, when they come home, taking care of them and getting them ready for bed, and then working again after they're in bed. And so it's just finding those moments, finding those opportunities, and also having a great team around me who supported me and leaned in and helped where they could help. And then also it forces you to kind of look at your business to say, "Okay, what am I doing that I can optimize in other ways?" Instead of getting on and doing every single sales demo, because at the time I was the sales team and our business doubled, by the way, during that terrible year, it doubled. So it was, it was pretty crazy. And so it's like, "Okay, I can do a video that does the initial demo. And then if people have questions, then get on the call with them." So it's just looking at ways to optimize what you're doing and to get more done that way.

Susan Sly 22:50:
That and while this is going on, Emily's going through chemo, your husband gets diagnosed. Was he symptomatic? What kind of cancer did he have?

Karen Gordon 23:01:
Colon cancer, and he's unfortunately still dealing with it.

Susan Sly 23:05:
Oh my gosh. Well, I will add him. I have a very extensive prayer list. And what were his symptoms? Because in colorectal cancer, I'm just going to do a PSA for a minute. So prior to artificial intelligence, my background was holistic health for many decades. And so in Canada, colorectal cancer is the top killing cancer, was the top killing cancer. And often people don't have symptoms. Did he have symptoms?

Karen Gordon 23:35:
He did. And he ignored them. He self-diagnosed. And finally, it just got to the point where, you know, he was having so many stomach issues that we couldn't do anything. We couldn't go anywhere. And we were actually headed to, because I just put my foot down and I said, "There's my friends, we're having a party that's an annual party, I really wanted to go there. It was three hours away." And we get on the road to go to this party. And I could tell he was absolutely miserable. He was in pain, he was not feeling well. And I said, "Look, you're either going to the doctor or I'm divorcing you, like something is wrong here." And so when they did the colonoscopy, they immediately saw the, you know, there was a tumor and kind of started this journey. And yeah, so it's been a long haul with that one.

Susan Sly 24:20:
And there was one night, some of the listeners who've been longtime listeners have heard the story, but I had been, I was in LA for a speaking event. And the night before, I'm in the hotel and I'm flipping through and it was A&E Biography, it was Natalie Cole. And she said the most profound thing I think I've quoted so many times that there's an old church saying, "You only see the glory. You don't know the story." And I remember thinking about that and how often do we see, especially, you know, what people who are leading, women who are leading, men who are leading, and you don't really know what's going on. They're just looking at the results. And what are they, you know, how's the company growing? And you know, all of that, but what's going on behind the scenes? And so I, you know, kudos to you, my friend. If no one has told you today, like seriously, it's absolutely incredible. You said something really interesting about the employees, setting the goals quarterly and flexibility. And there's this whole movement, you know, bring people back to the office and people don't want to go to the office. And I know I personally don't want to be in an office. Like I just, I don't. And so what do you, what is your philosophy on that? Because it's tough to say flexibility and then also say, "Well, you have to be in an office nine to five."

Karen Gordon 25:54:
You know, my first company was started around 2000. And we were remote back then. We had no Zoom, we, you know, we didn't have all these great things that helped us with that. I was just on the phone all the time. I was in Florida, my employees were mostly in Dallas, and my customers were global. And so my first workforce, because it started with just me doing documentation and training. And then as I kept seeing more and more opportunities and picking up more and more contracts, I looked for an untapped workforce. And that untapped workforce were women like myself who had actually stepped out of the workforce. They were trained, they knew what they needed to do, but they wanted to be there to send their kids to school and when they got home in the afternoons. And so when I brought that first group of ladies on, I basically told them, "I don't care if you work from midnight till 8am, as long as you get the job done with high quality and you get it done on time." And so I've always been of the philosophy if, as long as you have great communication around expectations, as long as you have great support, as long as you are open and willing to connect with your employees, they'll get their job done. And they'll do it happily. Actually, one of our employees just wrote an article recently that was in Authority Magazine. She's a, it's actually my youngest daughter, I'll say that. And she's very big on work-life balance and, you know, not living to work, but working to live. And so she just wrote an article about that, about how this next generation, that's what's important to them. It's not about climbing the corporate ladder, it's about enjoying your life during the time when you're also working.

Susan Sly 27:33:
Absolutely. And those boundaries become leaky boundaries, right? Like even for myself, our youngest daughter is 14. And I drive her to school every morning at 7am. And so people will say, like, we have, you know, we're doing our DevOps, we have some overseas folks, domestic folks, East Coast folks, like, "7am, can you meet?" And I'm like, "No. No, I can't. The answer's no." It's the, who said that song? Meghan Trainor. My name is no. My, like, I'm like, "No, no. I'm CEO of the company. And the answer is no." And I think that the piece I would say is that you actually become more productive when you're clear on your boundaries because the work gets done, you know, when you're aligned, when you're focused, when you know what that goal is. Even last night, one of our team members, he, yeah, we're building a company, so a lot of people are fractional, right? And so he's got other things going on. But, you know, I said at the beginning of the day, I said, "One goal is this," and he's like, "We're getting it done." And at nine at night, it got done. But that's okay. Like, it doesn't matter as long as it gets done. So I want to, I want to bring us to the present moment and talk about Simpli5. And, you know, I'm pouring on the website and I'm like, "Thank God," right? So what, you know, where did this concept come from? And what gets you up in the morning now and brings you that excitement, Karen, to keep building? Because you've been an entrepreneur for a long time and endured, you know, on the parallel path, everything that's going on with your family.

Karen Gordon 29:23:
So the core methodology was developed by a gentleman named Mike Stern, and Mike was focused on education. He focused initially on students in Maine who were labeled as learning disabled. And what he recognized, as he would say, is that he was teaching disabled. He was teaching like everyone else was teaching according to the industrial model of education, which does well for students who are high examine, high execute, detail-oriented, rote memorization, you know, they can get things done, but it didn't serve those students who learned in a different way. Maybe they need to see the big picture before they can focus on learning facts. Maybe they learn by connecting and sitting with other people and having conversation and restating concepts. And so he began to understand and look at where they got hung up in the learning process and where they moved smoothly. And once he started teaching to where they moved smoothly, they improved three grade levels within a nine-month timeframe. And so it was phenomenal. So he had, like I said, no desire to focus on anything corporate America. But what happened is the parents of those students saw the benefits. And then they would say, "This is great to get people unlocked and to kind of understand what they see and what they miss. Can you come and do a workshop with my team at work?" And so that's really kind of how it got pulled into corporate America. But we still have a product that focuses on learning. And we're still seeing phenomenal results from that, including a seven-year longitudinal study that followed these students after they went into the workforce. And these are students who were at risk, underprepared college students. I mean, many had come from just horrible situations, many had been in jail, many had been in gangs, but they were able to successfully go through a community college program initially. And what we saw seven years, we didn't do it. This was like a third-party company that did this analysis. But what they saw is that they were making 60% more than their counterparts who had not had the benefit of going through a program that included our methodology. The program was not 100% our methodology, but it was a big piece of it.

Susan Sly 31:28:
That's incredible. And so now, like where you're sitting, give everyone a purview sort of into the company. You know, how many team members do you have? Who are your ideal customers? Like, what is the next step for Simpli5?

Karen Gordon 31:46:
Yeah, well, as you know, within the company, the biggest challenge is trying to decide where to focus your energies, but especially in a smaller company. And so the challenge with our methodology with Simpli5 is that it has benefit everywhere. It has benefits for an individual, for personal relationships, for learning relationships, and at every level of an organization. Anywhere you have one or more people working together, there's value. But we've really had to focus on those customers who use this in a systemic way. So they have 1,000 employees or 25,000 employees that are utilizing the methodology. They use it as a common language, and then they apply it in many different ways, whether it be onboarding or conflict resolution or team collaboration or leadership development, there are ways to apply it. But as a SaaS company, you certainly want an organization that understands how to use this in an ongoing way because you want them utilizing this thing that they've invested in not just once or twice throughout a year but every single month as they're building that into other pieces. And so that's our ideal customer is an enterprise customer that has, you know, 1,000 employees or more.

Susan Sly 33:05:
Okay, so in terms of that piece around a company, right, it's like one of the challenges of success, if we could call it that, is where do you focus, as you said. You know, you have an incredible piece of technology, and it is applicable in so many ways. And we see companies that over-diversify, then we see companies that go too narrow, and there's that sweet spot of timing in terms of all sorts of things and getting tailwinds. And my final question for you, Karen, is you have, you continue to climb the mountain and charge the mountain as a leader in femtech, as a mom and a grandma and a wife. What advice, just if you were sitting down and having a cocktail or a coffee with another founder who's going through some very tough challenges right now, what advice would you give them?

Karen Gordon 34:08:
You know, I mean, it'll sound self-serving, but honestly, it's about knowing yourself, knowing what your strengths are, and then recognizing what you might be missing. Because again, none of us see everything. None of us are focused in all of the areas that are required to make a business successful. So, you know, whether it's a first-time founder or someone who's been in business for years, I just can't overstate the importance of understanding the way that you see things, the way that you move through processes. Because we know with building a business, it requires all of the phases of a project that we've discussed. It requires not only having great ideas, but being able to communicate those great ideas, being able to turn those great ideas into detailed plans that other people can then follow and help you to execute on, and you need all of those elements. And we all have preferences as to where we focus our time and our energy, and some of us, we love the beginnings, but we don't love the endings, you know, and we don't have energy for that, it's not as interesting for us. So we need to put somebody on our team that's going to focus on those endings to make things happen. So to me, that's the most important thing. And I see that with, you know, we've worked with Global 1000 CEOs across the world. And we've looked, you know, are there common energetic preferences, and there aren't. But the one thing that they all have in common is that they understand themselves, and they surround themselves with people who complement their energies, as opposed to people who are just like them, which is what is the natural tendency we want to do because it feels good to be with someone who thinks the way that you do and moves through the world the way that you do. But those aren't the people that you need the most. You need the ones who are completely opposite or complementary is really what we like to say.

Susan Sly 35:49:
And that's beautiful because you think a lot of times when people are choosing co-founders or they're choosing leaders, you know, they're their directors and above, they look for those similarities and not necessarily what's going to complement them. Because if everyone's putting their energy in the certain area that does really excite them, then a lot of things are lacking. And it's like you said with Mike and acquiring the IP, I've known many Mikes that, you know, they love research and data, but don't put them in front of a customer, don't have them, you know, go out and do pitches or anything like that. That's not their strength. And we need all of those strengths surrounding us. So Karen, you wanted to jump out and say something?

Karen Gordon 36:35:
Oh, I was just going to say, you know, one of the people that Mike helped to get unstuck was Doug Engelbart. And since you're in the tech space, you probably are aware of who Doug is. But he's the one that did the mother of all demos, and he created the mouse. I know IDEO perfected it, but he created it. And Doug was getting stuck because he was so high in what we call explore, this ideation phase, that he only wanted to surround himself with people who were just like him. But then that meant he was having trouble getting buy-in on his concepts because he was so far out there. They were so creative and so ahead of their time. And so he brought Mike in, and Mike helped to get him unstuck and to make him realize that he needed these people that he kept firing. He needed them because they saw it a different way. And they would help him to bring these products to market. And when Mike passed away, Doug was at the service, and he credited Mike with really helping him get unstuck in his career. So it's amazing the power of that methodology.

Susan Sly 37:38:
And so can people who are small business owners or solopreneurs, can they use the Simpli5 system as well? Or is it just for large companies?

Karen Gordon 37:46:
No. So what we did is we, instead of just ignoring that segment of the market, we created a self-service product. And so it starts with a conversation with one of our salespeople to kind of understand the size of your organization and what you're hoping to do. And then if it's the right fit, then we'll move them into the self-service org, and they're able to buy the licenses that they need, and they get emails throughout the year to kind of help them to understand how to apply it. And there's online training that's built into the software. So absolutely, we have something for everyone. But we just, you know, we spend the most of our time and our energy with our enterprise customers.

Susan Sly 38:17:
So yeah, that makes so much sense. And I love that too. It's like when you have something that can benefit so many people, to get it away from, you know, how does a big company ever exist? It started with someone's idea who was a founder who started and they gutted it out. They defied the 90% failure rate. And they grew it, and to be able to say, hey, we can serve this community as well. We don't have to manually serve the community. And it's so smart, Karen, but we can still serve that community. It's brilliant. So for everyone listening, I encourage you to go check out the Simpli5 website. There's a link to it in the show notes. And Karen, I just want to commend you for your brilliance, for your vision, and your tenacity, sister. I mean, seriously, I think that just from the bottom of my heart, you know, that resilience, mom to mom, wife to wife, and that you're still out there giving and serving is just tremendous. So thank you so much for being here.

Karen Gordon 39:18:
Well, thank you, Susan. I've enjoyed the conversation. Appreciate your time.

Susan Sly 39:21:
Well, thank you. All right, everyone. Well, I hope you love the show. Go ahead and tag us on social at Raw and Real Entrepreneurship, share the show. And if you have a comment or a question, go ahead, go to I read them all. And with that, God bless, go rock your day, and I will see you in the next episode.

Susan Sly 39:47:
So it is startup diary time, friends. And these are unscripted. This is really just me, whatever is on my heart to share in terms of the journey of founding a new startup. And in this episode, I want to talk about the power of saying no. So I have just interviewed Karen Gordon, who is the founder of Simpli5, and she has been through tremendous challenges. She, at one point, her daughter is diagnosed with cancer. She's a CrossFitter. She has a fall, and she thinks she's just got a bruised tailbone, and she ends up having a massive tumor and a rare form of cancer. And then while she's caring for her daughter who's going through chemo and her grandkids—her daughter's a single mom—her husband gets diagnosed with colon cancer, and now she's caring for him. And during this time, Karen talked about how she was able to just, you know, take care of her family but also be able to build her business. And I asked her, I said, you know, how did you set those boundaries? And she said, you know, I was taking my grandkids to school, then I was working. But I surrounded myself with a team who have strengths, and flexibility is so important to us. And we set our goals quarterly, and people have the flexibility as long as they produce the goal. And that really inspired me as a founder because right now, in terms of building technology, if you've ever been in charge of a product build, there are a lot of nuances to that. So you're spinning up environments, so technological environments, so it might be an environment on AWS or Microsoft Azure. As an example, you are getting a new GitHub license, you are, you know, you have Jira, you have all these different tools. And there's usually one throat to choke. So someone who is the master admin on all of those things, and then suddenly the notifications and there's multiple meetings, and you might be using a dev team to save money that is overseas. And so you're, there are a lot of pulls on your time, plus you've got to raise money, and you've got to sell. And perhaps, like me, you have kids at home right now. Three of the kids, three of the four kids are home for the summer. And then you also have aging parents, like I do. And so with everything going on, it's tempting to be a "yes-a-holic." And when you're a "yes-a-holic," it means that you're saying yes to every meeting, every demand on your time. Someone changes a meeting, and it's not convenient for you, and you're saying yes, and you're driving your kids to school, and you're on a meeting, and you're supposed to be sitting at the bedside of your aging parent, and you're in a meeting. And for me, I just didn't want to do it that way. This time, I wanted to be in a place where I was getting to do my meetings and getting to be present and getting to serve the people that I wanted to serve and not having this sense that I'm over-scheduled and over-programmed. So saying no is not easy at times because there is this whole FOMO piece. But if you say no, you actually respect yourself more. Because when you're the one starting the company, you know, just because someone's asking for a time, it's convenient maybe for them, but it's not convenient for you. It's okay to say no. It's okay to set boundaries. It's okay to say I know myself, and I'm true to myself. And I know that in order for me to perform my best, there are certain things that need to happen. And that time optimization is key. When I wrote the book "Organize Your Life" back in 2015, I spoke about this. We all have different times of the day when we have the most energy. For me, it's the morning. I make the best decisions in the morning. I'm clearest in the morning. But in the morning, for me to get to that place, there are three key things that I need to do. And one of the key things is taking about 45 minutes to pray and meditate. And then the second key thing is to be able to go and get some form of cardio workout in. And I'll do weights later in the day. And the third thing is to send out gratitude messages to my husband and kids. And once I do those things, then my head is on straight, and I'm ready to be the CEO and founder that I need to be for my team, for the investors, for our partners, and so forth. And so I had to get to the place where saying no was okay. And it wasn't about that. I, you know, was being a person who is inflexible. I give a lot of other options. But it's saying no because I respect myself enough. And I respect the person that is wanting to meet with me enough that they deserve for me to be 100%. And I'm not going to be 100% if I haven't done the things I need to do to be in the right headspace, and I haven't done the things I need to do to be able to prepare properly for whatever that meeting is going to be. So it's just some thought for you this week in terms of a startup diary, and I'd love for you to drop a comment below. And I'd love to hear if there's a topic you want me to talk about, go to, send a message. I have made a lot of decisions. And you're going to be hearing about those in the coming diaries about really guarding my time, about daring to pivot some things, and just even some strategic decisions. So anyway, thanks for watching this episode of Startup Diaries. And again, subscribe, drop a comment. I'd love to connect with you.

Susan Sly 42:58:
Hey, this is Susan, and thanks so much for listening to this episode on Raw and Real Entrepreneurship. If this episode or any episode has been helpful to you, if you've gotten at least one solid tip from myself or my guests, I would love it if you would leave a five-star review wherever you listen to podcasts. After you leave your review, go ahead and email Let us know where you left the review. And if I read your review on air, you could get a $50 Amazon gift card, and we would so appreciate it because reviews do help boost the show and get this message all over the world. If you're interested in any of the resources we discussed on the show, go to That's where all the show notes live. And with that, go out there, rock your day, God bless, and I will see you in the next episode.

Susan Sly

Author Susan Sly

Susan Sly is considered a thought leader in AI, award winning entrepreneur, keynote speaker, best-selling author, and tech investor. Susan has been featured on CNN, CNBC, Fox, Lifetime, ABC Family, and quoted in Forbes Online, Marketwatch, Yahoo Finance, and more. She is the mother of four and has been working in human potential for over two decades.

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