Matt Quammen WINS by Protecting Small Business Owners

Matt Quammen is the co-founder of Optimize Cyber, a company that specializes in cybersecurity services such as penetration testing and risk assessments. With a background in technology and sales, Matt brings a wealth of experience to the table, particularly in the realm of cybersecurity. His approach to the field is not just about the technical aspects but also about empowering business owners to understand and manage cyber risks effectively.

Optimize Cyber's mission is to disseminate cybersecurity knowledge at scale, ensuring that every business owner feels equipped to handle cyber threats. The company prides itself on speaking the language of business executives rather than tech jargon, making cybersecurity comprehensible for those without a technical background. This approach allows business leaders to implement practical solutions to protect their operations from cyberattacks.

During the interview with Carrie Richardson, Matt discussed various aspects of starting and running Optimize Cyber. He shared insights into the challenges of entrepreneurship, such as the difficulty of acquiring the first few clients and the unexpected ease of handling business operations. Matt emphasized the importance of having a clear mission and adapting the company's pitch based on market feedback to find the right niche within the vast cybersecurity industry.

One of the key takeaways from the conversation was the notion that cybersecurity doesn't have to be expensive. Matt pointed out that there are many free actions businesses can take to significantly reduce the likelihood of financial loss due to cyber incidents.   If you're wondering what you can do to protect your personal or business finances from fraud, don't miss this episode of WIN!

Matt also touched upon the value of partnerships, particularly with Managed Service Providers (MSPs) and Value-Added Resellers (VARs). Optimize Cyber has established a partner program that includes both reseller and referral options, allowing other businesses to collaborate without fear of competition for clients.

In terms of growth, Matt envisions Optimize Cyber expanding its consulting and product teams, continuing to produce high-quality offerings, and educating more people about cyber risk. He underscored the importance of tracking key performance indicators like revenue, pipeline, and new opportunities to forecast and plan for the company's future.

Overa

Carrie Richardson and Ian Richardson host the WIN Podcast - What's Important Now?

Serial entrepreneurs, life partners and business partners, they have successfully exited from multiple businesses (IT, call center, real estate, marketing) and they help other business owners create their own versions of success.

Ian is certified in Eagle Center For Leadership Making A Difference, Paterson StratOp, and LifePlan.

Carrie has helped create and execute successful outbound sales strategies for over 1200 technology-focused businesses including MSPs, manufacturers, distributors and SaaS firms.

Learn more at www.foxcrowgroup.com

Book time with either of them here: https://randr.consulting/connect

Be a guest on WIN! We host successful entrepreneurs who share advice with other entrepreneurs on how to build, grow or sell a business using examples from their own experience.

Chapters

• 0:00 Cybersecurity Entrepreneurship
• 9:38 Cybersecurity Startup Challenges and Growth
• 23:04 Optimizing Banking Processes for Business Leaders

Transcript

[00:00:00] Carrie Richardson: Good afternoon, everybody. My name is Carrie Richardson. I am a partner at Richardson and Richardson. And today I am your host for WIN what's important now. With me today is Matt Quamman, who is the founder of Optimize Cyber. Matt. How are you doing today? 

[00:00:15] Matthew Quamman: Doing great, Carrie. I'm going to have to switch that up to co founder, just to pay some respect to my co founder, but but nice to be with you.

[00:00:23] Carrie Richardson: Very nice. And what is the name of your co founder, please? 

[00:00:26] Matthew Quamman: My co founder is Stephan Dorn, one of the best ethical hackers in the world. 

[00:00:31] Carrie Richardson: Tell me a little bit about how Optimize Cyber came to be. There's two of you. One is one of the best ethical hackers in the world, and what do you bring to the table?

[00:00:40] Matthew Quamman: Pretty much all the boring stuff that we don't want the talented folks wasting their time with. I keep our books. I'm the finance side of the house. I run all our go to market and partnerships and sales. In a startup, you're always wearing a hundred hats.

[00:00:54] Matthew Quamman: So invoices, expenses, receipts, checks, bank accounts. [00:01:00] Drive into the P. O. Box. 

[00:01:01] Carrie Richardson: That sounds really exciting, Matt. 

[00:01:05] Matthew Quamman: Yes, it's glamorous. 

[00:01:06] Carrie Richardson: You definitely started a business to drive to the P. O. Box. 

[00:01:10] Matthew Quamman: Oh, it's the best part of my week. 

[00:01:13] Carrie Richardson: Tell me a little bit of how about how you came to start 

[00:01:17] Matthew Quamman: Absolutely.

[00:01:17] Matthew Quamman: I've been in technology the last 14 years. Eight years ago, I started in security and and fell in love with it immediately. Growing up, my dad had an HVAC company in small town Minnesota. Technology wasn't a big part of their business in 1991.

[00:01:33] Matthew Quamman: To me, cybersecurity is not about technology, cybersecurity is about protecting businesses and helping business owners like my dad avoid financial losses and When I learned that's what my job was when I got into security, I fell in love with it overnight. It's the most fun topic.

[00:01:58] Matthew Quamman: At almost every [00:02:00] happy hour gathering or neighborhood, talking to a neighbor. Everyone now has a story about financial losses, cyber attacks and has questions about it. I don't come from a technical background, but I've learned a lot from some very smart people that I'm able to share just practical solutions with my neighbors.

[00:02:17] Matthew Quamman: And Anyone I meet on how better to secure their business so that they can continue to operate safely and grow 

[00:02:25] Carrie Richardson: once upon a time. I was 1 of those people that use the same password for everything. I went to a. I can't remember the name of the vendor, but I do remember that Kid Rock was playing and it was in Las Vegas and I met a couple of Department of Defense security guys who had a little bit to drink and they walked me through how they would sell my house without me participating in any way at all.

[00:02:57] Carrie Richardson: And I left the party and I went up to [00:03:00] my hotel room and I changed the passwords on everything. And ever since I have been far more concerned with security practices. 

[00:03:10] Matthew Quamman: Yeah, unfortunately, those are true stories. And this is new to all of us. When I started in technology 14 years ago, it was largely not a conversation.

[00:03:20] Matthew Quamman: Security was very much an afterthought. All of us have learned the hard way, right? Small businesses, Fortune 500s Fortune 100s. They've all learned the hard way. That's what's also fun about cyber security is it's a dynamically changing field because we're all learning on the fly and we're all catching up to the bad guys and and trying to help business owners.

[00:03:42] Matthew Quamman: Prevent financial losses or help help people like Carrie in a Vegas casino avoid personal losses as well. 

[00:03:52] Carrie Richardson: I I didn't have that many personal losses that trip, fortunately. So cybersecurity is a really big [00:04:00] topic. I'd like to talk a little bit more about the business of cyber security and less about the technology that supports cyber security.

[00:04:09] Carrie Richardson: Tell me a little bit about what you were doing before you founded Optimize Cyber. 

[00:04:14] Matthew Quamman: So I've had a few different roles in the cyber security space some on the what we call MDR providers, where 24 seven, a technology company. A combination of technology and humans are watching your network and looking for bad guys and stopping them.

[00:04:33] Matthew Quamman: I've also been in the end point. I don't want to go down the technology rabbit hole, but it's a technology that prevents viruses from landing on your computer. And then I've been in the incident response space where somebody like you loses. Their title or wires a down payment to a house to the wrong people or businesses have a ransomware event or businesses wire money to the wrong people.

[00:04:57] Matthew Quamman: They would call. They call incident responders to come [00:05:00] in and find out what happened, try to stop the damage as quickly as possible, try to reverse the the financial fraud if they can and and get you back up and running safely. So through that I learned a lot about what can go wrong.

[00:05:15] Matthew Quamman: And conversely, was constantly thinking about, if and when I got back to the proactive side where we're on the defense side before an incident, what are some practical solutions that can help businesses avoid these types of attacks? So ultimately, after hundreds of cases in the incident response space, seeing way too many people crying about financial fraud or ransomware.

[00:05:43] Matthew Quamman: I knew I had to get back onto the defense side, right? The before an incident side. And by happenstance, I had this idea in my head for a proactive defense company and met the right guy to team up with who has the [00:06:00] technical chops to, to compliment my abilities very well.

[00:06:03] Matthew Quamman: And it just became a very good business marriage that we developed. First things first, you form the mission and then you form the products and then we started going to market. 

[00:06:14] Carrie Richardson: So what is the mission of Optimize Cyber? 

[00:06:17] Matthew Quamman: Our mission is to share cybersecurity knowledge at scale.

[00:06:22] Matthew Quamman: We want every business owner to feel empowered and understand cyber risk. What that means is a lot of people lump cyber risk or cybersecurity into the bucket of IT. That's not really the case. These are made up numbers by me, so take it with a grain of salt, but for illustrative purposes by my rough estimate, I'd say about 60 percent of cybersecurity is it related and 40 percent is how you operate as a business.

[00:06:53] Matthew Quamman: As business owners, we do need to oversee the IT side and make sure we have the right people that are doing the right [00:07:00] things on that side. But on the business operation side, these are very understandable processes like how you bank how you receive money, how you send money, how you double check that those funds are going to the right people.

[00:07:14] Matthew Quamman: Financial fraud is the biggest risk. Also, insurance purchases and things of that nature are really critical in this space. By sharing with business owners and business leaders, the fundamentals of cyber risk, we're able to empower them to make their operations more safe and to oversee IT security, which is more of the technical side in a coherent way.

[00:07:38] Carrie Richardson: And is this your first attempt at entrepreneurship? 

[00:07:44] Matthew Quamman: No, I mowed lawns and babysat many moons ago as far as professional I've had one man LLCs before where I've been a consultant to one or a few companies at a time. So this [00:08:00] is really the first time. 

[00:08:00] Matthew Quamman: We've built a brand, we've gone to market, we've gone all in on one venture in entrepreneurship.

[00:08:08] Carrie Richardson: What's the most unexpected part of being an entrepreneur? 

[00:08:13] Matthew Quamman: How many forms do you have to fill out just to run a business? Seriously, that's probably the biggest surprise. I don't know that there's been anything too surprising. I've been in, in sales management before and things like that.

[00:08:24] Matthew Quamman: I thought I had a tough stomach for the ups and downs and the rollercoaster that, that business can be, but entrepreneurship is that, Multiply by two or three so further callusing my hands and holding on to that rollercoaster has been a bit of a surprise, but Yeah, wouldn't trade it for the world.

[00:08:45] Carrie Richardson: And what part of you found the most challenging?

[00:08:48] Matthew Quamman: It's very difficult to get your first few clients, even though my co founder has over two decades in cybersecurity a ton of accolades and credentials. I have, nearly a decade of [00:09:00] experience and a lot of partners and a natural network.

[00:09:03] Matthew Quamman: It is hard to get those first several customers, but, once you get one dozen, the next five dozen is easier. And hopefully from there, the next. 500, 000 clients will be even easier for us. It's hard to go from 0 to 1. That's probably the hardest part, which I've never done before.

[00:09:21] Matthew Quamman: I've been at early stage companies, but to go from nothing on a. Yellow legal pad. I still like yellow legal pads and to name a company and get the website going and then get those first couple of customers that was a different journey for me and challenging, but also exciting and fun at the same time.

[00:09:42] Carrie Richardson: I started a joint venture six or seven years ago that didn't go anywhere and we were going through the basics. And I was getting really super frustrated with like how nitpicky he was about everything, right? The logo and the name.

[00:09:58] Carrie Richardson: And I was like, just come on, we have to make [00:10:00] money. This shit doesn't matter. And I didn't realize at the time that he had purchased a preexisting business. He had never had the opportunity to name a business or design the logo or do any of those things. So for him, it was a very exciting part of the business.

[00:10:19] Carrie Richardson: And for me, it was drudgery. Let's go. I don't care about the logo, we're gonna have to change it in five years anyway, just pick something that's suitable. It's a very interesting difference between someone who's already owned a business, started a business, versus that kind of initial excitement that comes from waiting for the graphic designer to send your stuff back.

[00:10:40] Matthew Quamman: Yeah, we got lucky on that front. We have a close connection who did phenomenal work on our logo. I love it. It was pretty quick and easy from that standpoint. The designer, a shout out to Tegan. She did an amazing job and it was relatively painless.

[00:10:56] Carrie Richardson: So the most interesting part so far [00:11:00] has been growing from one to two. The most challenging part has been growing from one to two. What was simpler than you expected?

[00:11:11] Matthew Quamman: The mechanics of operating the business. I've run a lot of the go to market pieces and Budgets on that side and made strategic decisions about where to spend marketing and event dollars . And I had always pictured that it would be much more difficult to run the operations, picking the technology we're going to use internally, picking the HR benefits and things of that nature.

[00:11:35] Matthew Quamman: And again, found some really great people to help. I found that to be much easier than I was expecting. And yeah, much, much simpler otherwise probably would have done this a while ago. Obviously there's bumps and bruises and it's difficult to start a business from scratch, but the operational burden's not as bad as as I was expecting

[00:11:55] Carrie Richardson: where have you seen your processes evolve for sales [00:12:00] operations, marketing, where have you seen the biggest lift 

[00:12:04] Matthew Quamman: I'd say you iron out your mission your pitch, your your sales deck of who we are as a company.

[00:12:13] Matthew Quamman: And then the market tells you what's important. So there was things we thought were very important that clients didn't. And things that we thought were less important that clients. I would say more than anything, just finding the niche in the market.

[00:12:26] Matthew Quamman: Technology is a big world. Cyber security is a big world. Our world within cyber security is a big world too. Finding that product market fit is a dynamic that constantly changes. We're not changing what we're doing. We're not changing the mission. Just how we educate new prospects has evolved over time.

[00:12:50] Carrie Richardson: Has your sales cycle changed as you've adapted to iterations and market feedback? 

[00:12:56] Matthew Quamman: It's hard to tell based on the, we have, [00:13:00] we're coming up on a hundred clients, but it's still law of small numbers.

[00:13:05] Matthew Quamman: I would say that our pipeline, our client fit has improved a great deal as we found our niche and found our revenue drivers that we can dump gasoline in and and land new prospects. New clients. The sales cycle itself hasn't changed too much. But we are reaching people earlier.

[00:13:24] Matthew Quamman: So I'd say we were generating more long term pipeline, which is really healthy. For us to be able to forecast and hire full time and to manage the business safely. 

[00:13:37] Carrie Richardson: So growth trajectory wise, where do you see optimize cyber in five years? 

[00:13:43] Matthew Quamman: Tough to tough to say.

[00:13:44] Matthew Quamman: Obviously, I'm biased, we're right up there with anybody else in terms of competence and in terms of, The services and products we deliver on the cyber security front. The growth has been phenomenal thus far. And if that continued, we'd be very large in [00:14:00] 5 years. But I got to think at some point, the growth trajectory slows down a little bit.

[00:14:05] Matthew Quamman: Where will we be in 5 years? We will have a very strong consulting and product team. That is producing phenomenal product and educating people about cyber risk. 

[00:14:18] Carrie Richardson: Are you monitoring specific key performance indicators in different areas of your business to ensure that happens?

[00:14:26] Matthew Quamman: Yeah. Revenues number 1 for us, but pipeline as well, new opportunities, new partners things like that to measure not just week to week or, month to month or day to day sales, but where the business is really trending. We track is new opportunities.

[00:14:46] Matthew Quamman: So new prospects new companies or new referrals from partners. And then the dollars that go along with those referrals as well as obviously closed revenue. Those are the biggest metrics for us. 

[00:14:57] Carrie Richardson: Are you an optimistic forecaster or [00:15:00] conservative forecaster? 

[00:15:02] Matthew Quamman: I'm a terrible forecaster, frankly.

[00:15:04] Carrie Richardson: So, optimistic! 

[00:15:05] Matthew Quamman: When I've worked for other people, I've let them tell me how to forecast things. I'm very much a percentage based, probability, predictor. And I will put my gut probability in there, and I think I'm fairly accurate with that. But if we have 10 deals that are all set to close by the end of April, I like to put a percentage in there of this one's a 20%, this one's an 80%, this one's a 50 percent because nothing's done until it's signed.

[00:15:33] Matthew Quamman: It helps you get the approximate value that you're expecting without having to, call your shot like Babe Ruth. It's a turbulent market right now, for sure. There's been layoffs there's a lot of businesses are looking to save money, which in some ways benefits us, but in some ways can delay deals as well. The goal here is to do as well as possible and to do the best job you can. And if somebody did the best job you can, and they don't sign, [00:16:00] you got to live with that. Conversely, sometimes you do a terrible job and they do sign. You got to live with that too, but that's the fun part.

[00:16:06] Matthew Quamman: And all you can control is trying to do the right thing on a day to day basis. 

[00:16:10] Carrie Richardson: Do you follow a specific sales methodology or a strategic planning methodology. 

[00:16:17] Matthew Quamman: Yes, I'd say it's cobbled together. When I started at Oracle, we trained on MEDDIC metrics, economic buyer, decision maker, decision timing identified pain, and champion.

[00:16:32] Matthew Quamman: I don't systematically ask those questions, but I do try to Check all those boxes and make sure that we know all the everything we can know about a deal and that we answer every question they may have. I was also trained on the pain funnel, which can be useful. Sometimes people don't want to sign up to delve into their pain.

[00:16:52] Matthew Quamman: So you gotta pull out of there quickly. It's a bit of a mishmash right now. And as we grow, these are things I'll have to solidify [00:17:00] and document for other people, but we're not there yet in terms of any formal methodology. 

[00:17:05] Carrie Richardson: Do you document?

[00:17:06] Carrie Richardson: Or is that something that you just rather push off to someone else? 

[00:17:11] Matthew Quamman: I would much rather push it off to someone else. I am competent though if I have to do it, and I do need those notes, right? We're running high velocity right now and I need those notes to refresh me on conversations from three, six, 12 weeks ago.

[00:17:27] Matthew Quamman: So I like documenting useful information. I hate check the box document information, which is why I don't do it. But yeah, absolutely. I'd rather. Push that on to somebody else and have someone here to take those notes once that's a financially prudent decision. 

[00:17:43] Carrie Richardson: You mentioned that being able to forecast helped you predict your talent requirements, have you got a prescriptive onboarding process already, or is it something that you're working on as a growing business?

[00:17:59] Matthew Quamman: We [00:18:00] have it. My co founder luckily has managed teams of dozens at a time, hundreds in total, offensive cybersecurity folks by offensive, we mean before incidents and proactive in nature. So he's onboarded a lot of people and train them up. And we we have a really good plan around that.

[00:18:20] Matthew Quamman: Ultimately, none of our stuff is necessarily emergency. Some people have deadlines that are, end of the week or a week out and those can be challenges to meet. But most people are shopping for their penetration test, their risk assessment, months in advance.

[00:18:35] Matthew Quamman: We're able to fill up the calendar for the capacity we have now. And then, As we need more capacity, hire and train more capacity without necessarily throwing them into the fire on day one, they'll have weeks to to ramp up and train.

[00:18:49] Carrie Richardson: What type of employee is the most difficult to onboard and manage? It sounds like you guys do really well with technical assets. How are the fluffier [00:19:00] roles within the organization? 

[00:19:02] Matthew Quamman: We haven't hired any fluff yet, so I'll come back on in a few months and I'll tell you about everything I screwed up onboarding them, but we're not there yet.

[00:19:15] Carrie Richardson: All right. Do you want to tell us the pitch for Optimize Cyber? So if somebody's listening today and they might require your services, who is your ideal customer? What are they looking for? And how do they find you? 

[00:19:30] Matthew Quamman: Absolutely. Our mission is to share cyber risk knowledge with business leaders and owners.

[00:19:36] Matthew Quamman: A lot of folks I talked to say this keeps them up at night and it shouldn't. This is a very manageable risk. All the things Carrie just grilled me on are much bigger risks to the company, bad hires and running, operating poorly and things like that. Those are much bigger risks than cyber attacks, but everyone tells me that one of the biggest concerns they have is cyber attacks.

[00:19:59] Matthew Quamman: If you [00:20:00] don't know where to start or if you've done some security but don't really have a strategy behind it or want to see how you're doing those are really. Where we operate best. This will not be a. Ones and zeros. This will not be a technology and coding conversation, and it's not pass fail.

[00:20:17] Matthew Quamman: We speak business executive and we make things comprehensible for a non technical audience to help you manage and prevent as many cyber attacks as possible. If you want to get in touch with us, optimize cyber dot com is the easiest. Carrie gave me a 2 hour SLA. If you reach out via the website, I'll get back to you in 2 hours.

[00:20:41] Carrie Richardson: Thank you very much. Matt. I really appreciate you coming on and telling us a little bit about how you're building and growing Optimize Cyber. Any last thoughts that you'd like to leave us with today? 

[00:20:53] Matthew Quamman: One last thought when people hear cyber security, they think it's expensive.

[00:20:59] Matthew Quamman: There's a lot of free [00:21:00] things you can be doing today as a business or business owner business executive that can drastically reduce the likelihood of losing money to a cyber attack. So don't worry about, hey, we don't really have the budget for this. There's a lot of free things you can be doing today.

[00:21:16] Matthew Quamman: And And we'd love to meet you where you are in your journey. So that's the last thing I'll put out. Don't think you need to have tens or hundreds of thousands of dollars set aside to, to secure your company. There's a lot of free things you can do today. 

[00:21:28] Carrie Richardson: What do you think the most important free thing?

[00:21:30] Matthew Quamman: Right now where do you bank is the most important thing that you can do for free. You need to have a relationship with a bank where, you know, them, they know you you've gone in and set up some offline processes, you've set limits around your ACHs, you've turned off international wires or limited wires to the extent you can and then put in notification settings.

[00:21:53] Matthew Quamman: So if money leaves the account, you get a text message for when the day happens that fraudulent money leaves the [00:22:00] account, you can get on it quickly. Because a murder case, it's the 1st 48 hours and you're going to be in a much better situation if you can get on this quickly. Most important that you can do as a business leader is tighten up the processes and how you bank with your credit union or regional bank.

[00:22:20] Matthew Quamman: And obviously those are free to set up with With your bank, you just need to spend the time to do it. 

[00:22:26] Carrie Richardson: All right. Thanks so much for spending some time with us today, Matt. I really appreciate it. And if you'd like to get in touch with Matt, you'll find all of his information in the show notes .

[00:22:36] Carrie Richardson: So thanks again, Matt. Have a great afternoon. 

[00:22:39] Matthew Quamman: Thank you, Carrie. You too.