Roselle Safran helped keep us safe at Homeland Security in the computer emergency readiness team and then the Obama White House before she took flight as an entrepreneur, now with two successful companies. President of cybersecurity company Rosint Labs, Roselle illuminates the path for anyone who wants to make the leap, from how to bootstrap and raise capital to the mindset you need to succeed.
Melinda Wittstock: Roselle, welcome to Wings.
Roselle Safran: Thank you, thank you.
Melinda Wittstock: It’s great to have you on and I’m really curious, what inspired you on your entrepreneurial journey. Let’s start at the beginning of the start up story for your current business.
Roselle Safran: Yeah so, the current business I’ve been at for less than a year now and I do cyber security consulting work. And before that I also had a start up that was doing cyber security on the product side. So, the two have gone hand in hand very nicely. Now, as a consultant providing services, I have the opportunity to sit down with the enterprises that I’m working with and government agencies and learn about their aches and pains and try to help with that.
It’s been great because I’ve been able to apply all of the past experience I had being in their shoes and essentially giving back, in a sense. And that’s been really rewarding and really enjoyable too, because it’s a very different type of work when you’re just providing your guidance and your recommendations and then letting that flourish in its own way.
Melinda Wittstock: Yes. I mean, all the great companies and services and products start with solving a problem. And so this is a problem that you were experiencing yourself in another life before you went out and said, “Okay, I’m going to be a cyber security entrepreneur.”
Roselle Safran: Well yeah, so before I decided to become an entrepreneur I was working on the operational side. So I was first working at the Department of Homeland Security in the division called USCERT, the United States Computer Emergency Readiness Team. And so the mission of the organization is to improve the security posture of government agencies and critical infrastructure companies. And so, in that role I was managing an office team and the work that was being done by my team was helping individual organizations and also the community at large.
And then from there I went to work at the Executive Office of the President during the Obama administration. And I was managing cyber security operations there. So, defending the network used by the White House.
So I’ve had a ton of experience in these operational roles where [inaudible 00:41:15 on living and breathing the exact problems that my current customers have.
Melinda Wittstock: Yeah, so what are some of the biggest challenges? I mean, obviously this is so much in the news, whether we’re talking Equifax or collusion in a certain America election, right? And so …
Roselle Safran: Yeah.
Melinda Wittstock: And so obviously cyber security is a big issue. You know, whether it’s the whole mess at Equifax or every now and again in the headlines you read about a company that’s had its security breached and a whole bunch of personal information is out there and on the dark net and all around. We’ve got all identity theft; we have the whole issue of a certain American election last year; a lot of stuff going on. So, your clients, what are their biggest problems and what do you help them with?
Roselle Safran: Well so one of the big problems is always just not enough resources, and no matter how big the team is, no matter how big the budget is, it’s just not comparable to the size of the fight. And it’s a really asymmetrical battle that any organization is facing right now, where the hackers have a real advantage because they only need to find one weak spot and they can make their way in. Whereas if you’re an enterprise, you’re defending a very, very large terrain and it’s an expanding terrain. In some cases you don’t even understand the breadth of the terrain because it’s not that clear and not that well documented.
So, it’s always is a challenge to create this trade off between what you want to prioritize and what you really have the capacity to handle. So I spend a decent amount of time just focusing on making sure that that foundational element is in place where even if they’re not grasping all of the challenges that they have to face, they’re at least getting the core problem solved now, in a sustainable way, so that they can start building on that as they move forward.
So that’s part of it and it’s just trying to make the most of the resources that they have, whether it’s on the technology side or on the team side.
Melinda Wittstock: Right, and so, I’m intrigued by this switch you moved from working at the White House, working essentially in government, to suddenly now running a start up, essentially, running a company. What were some of the biggest issues you faced, you know, personally in business, just kind of day to day work and making that transition from being, in effect, an employee to running a company?
Roselle Safran: Yeah, it was a totally different scene once I switched gears. The government environment is certainly far more stable. Despite occasional shutdowns! And it’s in some ways more predicable and in some ways slower, although, in cyber security nothing is really slow. And so it was definitely a huge transition.
But for me it wasn’t that challenging because I really enjoyed the entrepreneurial scene. I actually have no problem with uncertainty and instability. And I kind of enjoy it because I always look at it as a potential for opportunity.
Melinda Wittstock: Yeah, so it’s so interesting, Roselle, that you say that uncertainty is not something that bothers you. I think most people, you know, really struggle with things like uncertainty and change. But to be an entrepreneur, obviously you’ve got to embrace it. You’ve got to kind of like change. I know in my own journey, I love it that every day is different. I love being kind of tested around things, like I don’t know what’s going to happen today. And that’s kind of in my DNA, but it’s not necessarily in everyone’s. And so, making that transition, what were some of the lessons that you learned about it that you could share with a lot of our listeners who are, many of them are in the midst of that change or making, thinking about making that change, either from government or corporate, into the entrepreneurial world. And what are some of the things that they need to know before they take that leap or as they’re taking that leap?
Roselle Safran: That’s a good question. So, I guess my first thought would be, everything takes three times as long and costs three times as much. So if you have … At least. So if you have a pretty tight timeline in terms of how long you can go without a significant salary or how long, how much patience you have before you feel you haven’t made enough progress and you’re going to pack it in, you need to really factor in all of the uncertainty around it and recognize that even a realistic prediction, well, a predication that sounds realistic in your mind on day one, is not going to be realistic once all of the realities of the start up life come pounding in.
So, I would certainly recommend that the person take a long, hard look at how comfortable they are with just really having no idea what’s going to happen. No idea if the team is going to be put together in time, no idea if they’re going to be cohesive, no idea if the product is going to be finished in time or go down the road map that you’re initially thinking of and certainly no idea if the customers are going come through in the way that you want them to. Or if the messaging that you have in your head initially is going to really resonate. It’s all… it’s completely iterative, from day one until you get to some point of stability. And even then, there’s probably still iterative and so if that’s not something that sounds exciting … I mean, you can’t just be, “It sounds okay.” It has to actually sound exciting, because if it sounds okay on day one, it’s going to sound miserable after six months or a year.
Melinda Wittstock: That’s so true, especially when you think of, you know … Yeah, especially when you think of like, say, customers. So you go and you build this product, you have a great problem, you have a great problem to go solve or a big one, you know, big pain point. You have a big addressable market. You have all these things going for you. You have a great team, and so you go out and you create a product. The product is still a hypothesis. You still don’t know, you know, what the customers really want. So the, customer feedback is so, so critical. So when you mention iteration, really kind of having listening to what your customers want and meeting that need. So, give me an example of how you’ve had to be really iterative in the way that you’re building your business right now.
Roselle Safran: Well so, what I’m doing now is services, so there’s far more flexibility with it. And I’ve had the very good fortune of not really needing to do any sales. Because I’m established in the field at this point, so the opportunities tend to come to me. But certainly, when I was working at my previous start up where it was a product company, I had my initial ideas of what the product needed to be, based on my operational experience. But, even though I’d talked to a ton of my peers and I was very confident that I had a product that was really filling a gap, I still felt it was very important to have a large number of potential customers provide feedback very early on to make sure that I was on the right track with it.
So, I built out a very basic prototype early on and then had about 20 of my peers and potential customers give detailed feedback on it. And from that, then a beta was developed which used, incorporating all of that feedback. Because while I was on the right track with all of it, there were some features that were incredibly important that I wouldn’t have necessarily thought of just on my own. So 21 brains are better than 20, they’re better than one. And so once I had the 20 provided feedback, then the product took on a more well rounded aspect to it and so it became much more appealing and much more sellable just by getting that feedback really early.
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And it was important for us to do that long before we were trying to hit the market. Because once you have a product, your MVP is on the market, and then you try to iterate it and backtrack and make it something that’s palatable to customers, you’re creating all sorts of [inaudible 00:16:19 and you’re going backwards in a sense. And that’s … Time is never on your side when you’re an entrepreneur. So you always want to be able to get ahead of the problems to the extent possible.
And when it comes to product market fit and the messaging around how you articulate your value proposition, that all needs to start at the very beginning. You can’t just expect, “Oh, if you build it then they’ll come,” because that does not happen, unfortunately.
Melinda Wittstock: Yeah, a lot of entrepreneurs make that mistake, and I wonder whether it’s a fear, in a way. Of what the customer is going to say. I mean, the best thing to do is be talking to your customers, because that feedback as you say, you know, many brains are better than one. And I always scratch my head as to why you see some entrepreneurs really focus on build, build, build, build before the even talk to a customer. It’s probably better to talk to a customer first and then build. But what do you think that, what do you think holds people back from that? Is it just fear?
Roselle Safran: Well I certainly hope it’s not fear, because if you’re afraid to talk to customers you’re going to have a really uphill battle as an entrepreneur. I mean, I think it might be more of an issue of the person really understanding the space and thinking that what they have completely works. And yeah, occasionally that’s true, but often, you still are just coming at it from one perspective. And something that makes total sense to you might not be the same in someone else’s eyes. And it might not be the same in their environment. And so …
Melinda Wittstock: Yeah, I think it’s maybe it’s like, maybe it’s just attachment. Because I think a lot of people who do, do startups and they have this problem, and a solution they’ve come with, and all these credentials and you know, they know so much, they’re experts. But that doesn’t necessarily mean they know exactly what the market wants. And so there can be a disconnect sometimes.
Roselle Safran: Yeah.
Melinda Wittstock: I mean, I ask the question because …
Roselle Safran: Yeah, and …
Melinda Wittstock: Oh, go ahead.
Roselle Safran: I was just going to say, even if they know what the market wants, it’s an added layer of complexity to be able to effectively articulate that. And that I find to be one of the biggest challenges, especially if you’re in a highly technical field or a very crowded field.
Melinda Wittstock: Oh it’s so true of a crowded field. Oh my God.
Roselle Safran: Yeah.
Melinda Wittstock: That’s really tricky, because how do you stand out? And I think that’s an interesting challenge for women as well. Sometimes we struggle to sing our own praises. You know we’ve all been acculturated to kind of to hang back a little or to say, “Oh, you know, the team did it.” Or whatever. We talk a lot on the podcast about where women sometimes shortchange themselves in that kind of how do you stand out from the crowd or develop that thought leadership or personal brand or whatever that you need to really stand out?
It sounds like that hasn’t been a difficulty for you.
Roselle Safran: Well, I think that there are a couple issues at play. One of the issues that I see is tough for women in general, especially when they’re doing something like say pitching a venture capitalist. It’s that they don’t necessarily convey confidence the same way that a man does. And when they are pitching to a man, who is expecting a certain type of posturing and a certain way of presenting that matches their definition of confidence, there’s going to sometimes be a big discrepancy between the way a woman presents herself and the way a man present himself.
And so I see that as being a big challenge, almost more so than the concept of not blowing their own bugle. Although, I guess in some ways the two are related. But some of it is just the way that women, in general, of course I’m making a huge generalization here, the way that they present themselves might not exude confidence the same way that a man could potentially present himself and it’s not because they lack the confidence. And it’s not because they lack the capability. It’s just, they present differently. And …
Melinda Wittstock: We do talk differently and I think, you know, in all the debate around access to venture capital money, you know I think sometimes women go into the situation either with an addressable market that primarily, women, say, like in fashion tech or fem tech, that the men don’t understand. So there’s that. And then the other problem is just like, I think, yes, we just present a little bit differently.
I mean, have you had to go out and raise money for your company or are you more of the bootstrap variety?
Roselle Safran: Yeah, so for my current company there was no need, with the services company that I have. Like I said, I had the opportunities coming in from day one. But for my previous company, the product company, I absolutely had to raise capital. I raised two and a half million dollars in seed funding. And it was quite a production. And after I left that company, one of the investors in my start up asked me to become the entrepreneur in residence for the firm.
So I’ve been doing that as well, for over six months now. So I’ve been seeing the other side of it, on the investor side as well. So, I’ve had my fair share of experiences in this area, and that’s part of why, that always comes to mind for me.
Melinda Wittstock: Yeah, so where do women go wrong? I mean if you’re … This is intriguing to me, you know because you have the view of both sides, I guess, of the equation here. And so, not only where do we go wrong, but where could we be better at really making the case? Like I’ve seen women with amazing scalable businesses, you know great kind of moon shot businesses or just like, with everything, their ducks in a row, and still had a hard time raising money.
Roselle Safran: Well part of it is who you’re pitching to. And there are just going to be some investors that have their investment pieces and they don’t stray from it much. So they have a certain type of company, a certain type of founder that they view as the equation for success. And if you deviate too much from that, you’re just not going to be a fit for them.
And sometimes it’s completely related to the company and the market and it doesn’t have anything to do with the founder. But sometimes there is the founder component of it. I mean, I’m fortunate that the firm that I’m working with does not exhibit any gender bias. I think about almost half the portfolio has women founders and they really are focused on just the capabilities of the founder, not the gender, and the product, the market, all of the important factors.
But, with that said, you’re going to run into a decent number of investors that are just not that easy to pitch to. And it could become a very discouraging process, very early on. So you have to just develop a thick skin. That’s, I would say, almost rule number one, is just recognize the fact that you’re probably going to have, if you have a five or ten percent hit rate, that’s pretty good for a first time founder. And if you go into the conversation accepting the fact that you’re going to do as well as you can, you’re going to learn from each experience so that you’re better the next time, but chances are it’s not going to work out, it become much more palatable.
And you can muster up the strength to go to the next one when you view it with that type of mentality. And this goes back to what I was saying about being iterative. It’s with everything that you do. You’re always trying to just hone that messaging and get it to resonate better. And so, instead of taking each no as a type of defeat, you can turn that around and say, “Okay. What can I actually learn from that experience?” Ideally, the investor that gives you a little bit of feedback as to why they decided not to invest, that’s actually super useful. Because you can potentially then incorporate that into the next pitch.
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But, it’s not an easy process for anybody. And there is definitely some added challenges if you don’t … But in general, again, these are generalizations here, in general, if you don’t look like or have the background of the investor, it is often more challenging. But that’s not always the case, it really just comes down to who you’re talking with and investors are just like any other people. There are some really awesome investors and there are some really lousy investors and there is everything in between.
And it’s almost a numbers game in some ways and you can improve your odds as you go along if you just take every discussion as a learning experience.
Melinda Wittstock: Yeah, I think you mentioned a couple of things that are so vital. Like not taking it personally. And really just trying to find that fit. I mean, I think doing your research on the investment thesis. You know, who else have they invested in? What are the odds? And then getting that feedback.
The interesting thing about feedback though, I have seen some female entrepreneurs take so much feedback from investors and the feedback is contradictory. So much so that they’ve kind of lost their own way, you know, with their startups. Even to the point of you know, pivoting maybe too soon, before they’ve really disproven something, because we’re so open to taking advice right? So like where is that, where is that fine line, right? Between where feedback is great and feedback is too much, it’s going to get you off your game.
Roselle Safran: That’s a great question, because that, it’s so true that you could be talking to two different people, both very experienced with great, relevant backgrounds, and they can give you completely opposite advice. And …
Melinda Wittstock: Oh my God, that’s happened to me so many times.
Roselle Safran: Yeah. Yeah, yeah. That’s very common. And yeah, it’s tough, especially when you’re just starting out and you’re just trying to establish your own grounds to figure out which advice you actually incorporate and which maybe put to the side. And so at the end of the day, it really comes down to the entrepreneur herself having a strong core sense of confidence and the ability to evaluate advice as it comes in. Because no piece of advice that comes in is going to have all of the context that you have about your company.
So, when some … Advice comes in you have to almost filter it against what you know. Which could be different and sometimes you want that other perspective because it’s not within the context of your company but it’s within the context of 20 other companies that were like yours. But at the end of the day it does, there is some filtering that needs to be done by the entrepreneur herself, that’s just based on what she knows, what she’s experiencing with her company. And in some cases, based on how helpful the person’s advice has been in the past. But yeah, it’s definitely, it’s a challenge to figure out which advice is worth following and which advice you just keep in the back of your head. But maybe don’t act on at the moment. And I’ve seen this go well and I’ve seen this go poorly.
I mean, certainly I’ve, now that I’m on the investors’ side of it, I see when entrepreneurs have been really receptive to advice and when they’ve almost gone in the complete other direction. And they just don’t want to take any advice from anybody. Because I don’t know, maybe they’ve heard too much advice and, or some of it’s been wrong in the past or they’ve had some other bad experience. But some entrepreneurs on the other end of the spectrum where they are only going to listen to how they feel and their decision and they’re not going to adjust course at all based on any feedback. And so, and that’s not healthy either.
So there’s definitely a middle ground, which is not particularly easy to find, and I think, over time, as you continue to grow and the company continues to grow, then it becomes a little clearer when the advice makes sense for your specific situation.
Melinda Wittstock: Yeah, so much of this is down to the mindset you have and confidence being in alignment with your own, I guess, not only values or purpose, but also your talent. So entrepreneurship does require quite a lot of self-awareness. I find that that self-awareness grows in the journey. I mean, where you are right now, Roselle, as opposed to where you were when you were starting out, do you feel that there’s been a lot of personal growth on this journey as well, as a result of the entrepreneurship?
Roselle Safran: Oh absolutely. Absolutely, yeah, I mean, you come out with an entirely new skill set and an entirely new way of evaluating so much of what’s going on around you in the business setting, that … To me that experience is worth it’s weight in gold.
And there has been a tremendous learning curve. I’ve made my fair share of mistakes. And I don’t feel that any of those mistakes were a problem at the end of the day because they all turned out to be great learning experiences. And what’s really most important for entrepreneurship is not avoiding mistakes, but being resilient. And being able to adapt when something does not go anywhere near as planned.
Melinda Wittstock: Exactly. I find failure as feedback. I mean it really is.
Roselle Safran: Yes.
Melinda Wittstock: Or like, #failforward. Because failure in effect, right, is learning. I mean, from everything that just happens, it’s like your life and your start up it becomes your lab. And I really, it’s interesting, you get to the point where you realize that there’s this correlation in a weird way between your business growth and your own personal growth.
And it becomes, the journey itself becomes fascinating, just being in the moment of the journey. There’s no … The destination, I think we get so caught up in the destination that we’re getting to that we forget to actually enjoy the path to that destination and all the ups and downs, but that’s where a lot of the joy and the creativity and the fun actually is.
Founders look back on the times when it was really, really tough and they were struggling to make pay roll or they were really figuring out the product and at the time it seemed really difficult. But those are the times that you back on and it’s like, wow, that’s where it was fun. That’s where I grew. So being able to be in the moment with it I think too is important.
Roselle Safran: Yes. Totally agree. Easier said than done when you’re in the middle of it though.
Melinda Wittstock: It totally is easier said than done. I mean maybe, I’m on company number four now right, so you like … What’s very funny and humbling about it though is because you think you’ve got it right, like, “Oh yeah, like I can do this.” And but there’s always something new. Like you’re always going to be tested in a new or different way.
Roselle Safran: Totally.
Melinda Wittstock: So it’s a very humbling process. So as we sort of start to wrap up, what are three pieces of advice that you would give to women who are either thinking of embarking on their entrepreneurial journey or they’ve had a long, more of a corporate career and they’re going to kind of switch over into entrepreneurship or they’re in that early stage, where they’ve gotten going but, oh man, now it’s time to scale or whatever. I mean, there’s different phases of this process, but what are your sort of three pieces of go to advice that we can leave listeners with today?
Roselle Safran: Yeah, well I guess I start with, that I’ve already discussed to an extent, the need for that confidence to come from within. It can’t be dependent on external validation because you’re probably not going to have that in the very beginning and there’s going to be a lot of failure and many people that are saying no in one shape or form or another. And so the, what propels you forward has to be your confidence in yourself and your capabilities and your business. And that, in my opinion, has to be the foundation for any entrepreneur and any business. So that answer would be number one.
Number two, I would say for women is that while it’s easy to think that trying to pick up male traits to act more like a guy, is really what will get you to a level of success, the way I see it, acting true to yourself is more effective. Because it’s usually, unless you’re a great actress, it’s usually pretty apparent when you are trying to act like somebody else. And so I always think that someone who is coming into a conversation with their true self is going to have a better chance for success because they’re not trying to predict what someone else is expecting. And they’re putting their true self forward.
This is the type of advice that you could probably hear the complete opposite of, depending on who you’re talking to. But, so much of entrepreneurship is built on trust. And you build trust when you are yourself. Not when you are trying to pretend to be somebody else.
And then my third piece of advice would be … It’s sort of along these same lines, it’s not to feel that you need to focus on what you perceive to be a weakness. And think, “Oh, well I’m not great at public speaking, so I need to spend all my time and energy on becoming better at public speaking.” Or something along those lines. It’s more important to capitalize on the strengths that you do have.
Melinda Wittstock: Yeah. And hire your weaknesses.
Roselle Safran: Exactly, yes. You can very easily figure out ways to compliment your capabilities and if you’re acting naturally and you’re confident in who you are, then you can say, “Hey, I’m not good at x. I’m not good at y.” And then yes, as you said, just hire someone who can round out the team in that way.
But what you are strong at, needs to be your primary focus on just making it stronger and leveraging that as much as possible.
Melinda Wittstock: That’s awesome. So Roselle, how can people find you and work with you? A lot of women listening to this podcast have businesses; they surely have cyber security needs. So how can folks find you?
Roselle Safran: Yeah, so Linkedin seems to be the easiest way to reach me. My name on Linkedin and also on Twitter, Roselle Safran, again, just my full name. And also my email address for my consulting company is roselle@rosintlabs. So R-O-S-E-L-L-E at R-O-S-I-N-T-L-A-B-S.com and I’d love to hear from any women that is interested in starting up a company or interested in going into cyber security. I’m more than happy to provide advice.
Melinda Wittstock: That’s awesome. Thank you so much for putting your wings on today and flying with us.
Roselle Safran: Oh, well thank you very much. It’s been a pleasure.