Jeremy Vaughan Raised a $3M Seed and Told Investors That Gave Him the Runaround...No
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4 Years of Blood, Sweat, & Tears Before Raising Their $3M Seed Round After Achieving $1M in ARR
In this episode, Jeremy Vaughan, a cybersecurity innovator and founder of Start Left Security tells us how he secured a $3 million seed round after 4 years of building his company and passing $1M ARR. He offers invaluable strategies and tips for fellow founders when it comes to raising from angels and participating in multiple accelerators.
His approach, from the initial grind through strategic partnerships to revenue focus, offers a blueprint for running a sales process for fundraising and business growth invaluable to founders at any stage.
Here's what you're in for:
03:04 - Challenges of scaling an EdTech company
05:37 - Fundraising strategy into raising $12 million in venture capital
17: 10 - Lessons learned in funding options
20:39 - Selling ClassTag
26:55 - Vlada's advice for new founders
About Jeremy Vaughan
Jeremy Vaughan got a finance degree at the start of the Financial Recession but turned into a tech entrepreneur who saw an opportunity to make the digital world safer. Founding Start Left™ Security, he created cybersecurity solutions for cloud-based applications. His philosophy is to stay ahead of threats by being proactive, not just reactive.
Start Left™ is revolutionizing SaaS security with its innovative, all-in-one security suite, that covers a business from start to finish, ditching the outdated, scattered approach for something way smarter.
Connect with Jeremy on:
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Jeremy Vaughn, founder & CEO of Start Left Security, shares a candid playbook on surviving the early years, turning channel partnerships into seven-figure revenue, and creating real investor FOMO—ultimately closing a ~$3M seed round in 2023. We cover angel checks, accelerators (Hartford InsurTech Hub, Tampa Bay Wave, UNF), simplifying complex security for SaaS SMBs, and lessons for running a disciplined fundraising sales process.
Jason Kirby: Hey, everyone. Welcome back to Fundraising Demystified. Today we have Jeremy Vaughn with us, founder and CEO of Start Left Security. Welcome to the show, Jeremy.
Jeremy: Thank you, good to be here.
Jason Kirby: Now I'm excited to hear your story and be able to kind of understand your lessons to share to founders on how you went about raising capital. So let's just jump right into it. Can you tell founders a little about you and what you're doing at Start Left Security?
Jeremy: I graduated with a finance degree, which gave me some chops to speak investors’ business language. When smartphones came out, I knew technology was where I needed to go. That was also the 2008–2009 recession. I moved into tech and have been a tech entrepreneur around software development for the last 16 years. We built Start Left Security over the last couple of years and brought it to market in 2019.
Jason Kirby: So you started in 2019 and you recently raised a seed round of around three million in summer 2023. That's four years. What were you doing in that time? What was the business achieving? How did you stay afloat?
Jeremy: Blood, sweat, and tears. I raised a small angel round from a local investor I’d known for years. I presented the opportunity and he said he’d always believed in me—so he was in. That belief changed my trajectory, and I’m incredibly grateful. Being in Florida, we didn’t have Silicon Valley money. My network was geographically limited, so I focused on growing it—joining accelerators to extend into the Northeast and across the East Coast.
If you track the timeline, that’s when COVID hit. I built relationships with investors then and told them I’d keep building. Nobody wanted to put money to work during that time. I had big deals lined up that would have unlocked investment, but COVID blew it all up.
Jeremy: I stepped back to educate the market, keep investors close, and form channel partnerships. I asked investors which metrics they wanted to see, then focused on hitting them—on product, revenue, and partnerships. Investors stayed close and watched us execute. I kept reminding them we were doing this with almost no money—imagine what we could do with a little cash. The channel network took 12–18 months to ramp, but by 2022 partners were sending deals. We got over $1M in revenue before starting the seed raise.
Jason Kirby: Early days: that first angel—was it only one check, or multiple?
Jeremy: One at the very beginning. It covered legal, launching the company, and building more product. We already had an existing product before that angel money—we invested in ourselves first. Many investors see founders not investing their own resources as a red flag. Later, a VC firm gave us a $50k bridge as we were about to close our first $150k LTV deal over two years. We closed it in about three months and turned that into more deals. We also received a small grant from an accelerator—enough to stay above zero and keep moving.
Jason Kirby: Which accelerators did you go through?
Jeremy: The Hartford InsurTech Hub (Startupbootcamp—now closed) where I lived in Hartford for six weeks until COVID shut it down; Tampa Bay Wave’s first cybersecurity cohort; and the University of North Florida incubator. Each added different value and networks, which mattered with everything shut down.
Jason Kirby: Totally. Those programs can be lifesavers outside major tech hubs.
Jeremy: Exactly. Our strategy targeted insurance because our platform functions like “insurance” for software companies’ security posture. Tampa Bay is also a cybersecurity hub—lots of cyber firms and activity—so plugging into that community was strategic.
Jason Kirby: You mentioned maintaining investor relationships and asking what metrics they wanted. How did you manage that over time?
Jeremy: Excel and lots of reps. I talked to hundreds of investors and built intuition on qualifying them—just like they qualify us. Founders should confidently “interview” investors. I focused on creating FOMO by setting quarterly check-ins: “Here’s what we’ll do by April—put time on the calendar.” I told them I was doing this with several firms and looking for true partners. Treat it like a sales process with clear qualification criteria and cadence. The ones who stuck around through the check-ins were likely to be good partners.
Jason Kirby: It also demonstrates founder-led sales—a skill VCs look for.
Jeremy: Four years is a long time. Early on, the market signals were murky. Big incidents like SolarWinds should have spurred immediate movement, but regulation lagged for years. As data points accumulated, our narrative got stronger—we could predict adoption timing. I told investors: high adoption year in 2024, major adoption in 2025–2026, and why. With better data, investors started following our lead.
Jason Kirby: Being a thought leader builds trust. You hit $1M revenue—was that when you raised, or did VCs come knocking?
Jeremy: Both. I’d tried to raise earlier but stopped—moving goalposts were frustrating. At $300k ARR: “Come back at $500k.” At $500k: “Come back at $1M.” If we don’t need you anymore, that’s when money shows up. Once we crossed $1M I decided it was time—and if people still moved the goalposts, I moved on. Near the end of the round, some who’d said no came back asking to put in $1M+, but we were closing. It was satisfying to say no after months of squirming.
Jason Kirby: Sweet moment—pick the partners you want. Moral: run a process and build a great, defensible, revenue-generating business. Capital then accelerates you.
Jeremy: Exactly.
Jason Kirby: What growth rate were you at around $1M when you raised?
Jeremy: Honestly I wasn’t tracking it closely then—we were keeping the wheels on. It was me, my CTO, and a director of engineering doing almost everything, plus a few contractors—4–5 people getting past $1M is hard. As we neared that mark, we added more help. Fundraising itself is a full-time job. With some capital, we could breathe and make things more repeatable.
Jason Kirby: You closed ~$3M—what happened next?
Jeremy: We stood up product operations and hired for product leadership. We spun up sales and marketing, aligning everyone on a simplified message. We were close to product-market fit at the raise but hadn’t completed the whole value prop. The last six months were a sprint to ship v2 and book Q1 sales. We shipped v2 in early January smoothly—new slick UI, clearer for non-security stakeholders. Sales is hard to scale—the founder can switch personas (DevOps, security, business) instantly; you can’t expect that from reps on day one, so we simplified scripts, demos, and value props.
Jason Kirby: What type of companies are you targeting—enterprise or SMB?
Jeremy: We can serve enterprise and have them in pipeline via partners, but our focus is SaaS companies (post-seed to Series A/B/C). Many point solutions eat an entire AppSec budget. We built a platform with multiple tools for a fraction of traditional costs, especially for SaaS SMBs. We help companies stay resilient and ready—from raising capital to audits to exit—so technical due diligence isn’t a fire drill that slows feature delivery.
Jason Kirby: That’s real value—I’ve lived the diligence chaos during an acquisition.
Jeremy: Exactly. Predicting market timing mattered. We’ve supported tech due diligence with PE firms whose portcos are software companies. Security is just good business now—it’s increasingly required. We’ve advised not to buy in some cases and helped increase valuations in others. Diligence aims to find devaluation points—like unresolved incidents. If a wide-open hole remains unmitigated, buyers walk.
Jason Kirby: Bigger buyers dig deep; cyber risk can outweigh deal value.
Jeremy: Right. Look at MGM going down—software failures can cost millions per day via lost availability. Traditional cybersecurity doesn’t emphasize uptime/availability enough. We enable proactive security to protect revenue and customer experience.
Jason Kirby: Where can people learn more about you and Start Left Security?
Jeremy: I’m on LinkedIn—Jeremy Vaughn (V-A-U-G-H-A-N)—bright pink profile pic. And visit startleftsecurity.com.
Jason Kirby: Parting advice for founders closing a seed round?
Jeremy: I used to avoid cybersecurity-focused VCs, worrying they saw the same decks and might share ideas. I got over it. You just need one strong lead with domain credibility. We brought in Ron Gula’s firm (founder of Tenable), then built momentum with others, including generalist funds. Ask VCs to help—warm intros to co-investors both protect their investment and show they’ll support you in the future. Shift your mindset on how you attack the raise.
Jason Kirby: If a shared deck can sink your company, the business wasn’t that strong. Put yourself out there to build relationships. Jeremy, thanks for joining us.
Jeremy: Thank you—love the show. Take care.
Start Left Security is a cybersecurity platform aimed at SaaS companies that consolidates key application security tools and workflows. It helps teams stay “resilient and ready” for audits, diligence, and incidents without slowing product delivery.
Jeremy invested personally, secured an initial angel check, a $50k bridge from a VC, and a small accelerator grant—then leaned heavily on channel partnerships to drive revenue through the COVID period.
Hartford InsurTech Hub (Startupbootcamp), Tampa Bay Wave’s cybersecurity cohort, and the University of North Florida incubator.
Quarterly check-ins with clear goals, consistent execution, and a running “qualification” process for investors—treating fundraising like a sales cadence. Once credible domain leads joined, other investors followed.
SaaS companies post-seed through Series A/B/C, with a need for consolidated AppSec capabilities at a cost that fits SMB and growth-stage budgets, while remaining scalable to enterprise needs.
Security failures that impact availability can halt revenue and degrade customer experience—sometimes costing more than traditional data exposure. Proactive security protects both revenue and trust.
Series: Fundraising Demystified
Episode: From Grit to Seed: Jeremy Vaughn on Funding Start Left Security
Guest: Jeremy Vaughn (Founder & CEO, Start Left Security)
Host: Jason Kirby
Core Topics: seed fundraising; investor relations; accelerators; channel partnerships; product-market fit; cybersecurity platform for SaaS SMBs; due diligence; availability & uptime; founder-led sales; creating investor FOMO.
Key Entities: Start Left Security; Hartford InsurTech Hub (Startupbootcamp); Tampa Bay Wave; University of North Florida incubator; Ron Gula; Tenable; SolarWinds; MGM.
Timeline Markers: Company to market in 2019; COVID impact 2020–2021; >$1M revenue by 2022; ~$3M seed round in summer 2023; v2 shipped early January (post-raise).
Takeaways: Treat fundraising like a structured sales process; qualify investors; maintain cadence; build revenue and defensibility; simplify complex value propositions for multiple personas; proactive security protects revenue.
SEO Keywords: Start Left Security, Jeremy Vaughn, Jason Kirby, seed round, cybersecurity startup, SaaS security platform, channel partnerships, investor updates, accelerators, Hartford InsurTech, Tampa Bay Wave, fundraising strategy, investor FOMO.
Host: Jason Kirby · Guest: Jeremy Vaughn
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