Not Another CEO Podcast

Most companies that start the FedRAMP process never finish it. Irina Denisenko built a business on getting you through it in 90 days, and said so, loudly, when everyone told her not to.Irina is the founder and CEO of Knox Systems, a company that gets software companies FedRAMP certified — the federal government's exhaustive cybersecurity authorization required to sell to agencies like the Pentagon — in 90 days instead of the usual multi-year process. Two years in, Knox has raised over $30 million, crossed 100 customers, and counts Adobe among them. Before this, Irina was COO of Class Technologies, where she had to get her own company FedRAMP certified and ended up acquiring an already, authorized company just to get through the process. She later spun that capability out as Knox.Here were my biggest takeaways:1. Trust that you know your market better than the room does: When advisors pushed Irina to soften her tagline, she refused. "I know my market. I've lived this problem," she told me.2. Turn a cost center into a revenue unlock: Irina assumed her first customers would come through CISOs. Instead, her first ten came from calling friends who ran companies. The real unlock was reframing FedRAMP: it's not a compliance expense, it's access to a market a company was previously shut out of entirely. 3. Make your investors work for you, even when you're not raising: Irina stays close to her investor network specifically because boardrooms are where FedRAMP tends to get dismissed as too slow to bother with. She's built a habit of asking investors to correct that in the room on her behalf. 4. Kill a bad bet before you defend it: Knox made an early bet on a specific AI approach to auto-remediate security vulnerabilities. The technology wasn't ready yet, and by the time that was undeniable, they'd already sunk real time and money into it. 5. Never underpay your best people: Irina calls her hiring approach "Delta Force" — senior only, nobody walking in without years of reps elsewhere. Her rule on comp: she's never once regretted overpaying for the right person, and calls the opposite mindset "pennywise, pound foolish."Quote of the Show:"If you know your market, you should know how to talk to them. And if you don't know your market, you go figure out your market first.” - Irina Denisenko, Founder & CEO, Knox SystemsGuest Featured in this Episode:Irina Denisenko: https://www.linkedin.com/in/irinadenisenko/ Knox Systems: https://knoxsystems.com/If you enjoy the episode, please like and subscribe on your favourite platforms and share with your network.We also break this episode down into a full write-up on Substack, with the exact playbook Irina used to build a go-to-market motion around a tagline everyone told her to drop, we're building out a full library of playbooks and lessons from every episode on Substack.Chapters:00:00:00 — Intro: Irina Denisenko & Knox Systems00:02:13 — The "FedRAMP in 90 Days" Tagline00:06:34 — Building In-Person Across 3 Cities00:08:52 — Hiring Only "Delta Force" Talent00:11:41 — Revenue Per Employee in the Age of AI00:17:10 — How She Vets a Delta Force Hire00:25:57 — Never Regretting Overpaying for Talent00:31:26 — Landing the First 10 Customers00:42:41 — Investors as Her Best Referral Channel00:47:43 — "Who Cares About This Market"00:52:31 — The Valuation Hangover01:02:16 — Scrapping a Year of AI Work01:05:29 — From the Soviet Union to Founder01:16:41 — Closing Advice: Integrity Above All

I've interviewed over 100 founders and CEOs on Not Another CEO. I've asked them about their hardest days, their biggest regrets, and the sacrifices they made to build what they built. I never thought I'd be the one in that seat.This week, my own kids flipped the mic on me. Sammy and Noah wrote their own questions and interviewed me for the show, and I had no idea what was coming. We covered the worst week of my career, firing people I actually liked, the sacrifices I made that I'd still make again, and the moment my son stumped two successful CEOs on a live stage with a single question.Here's what we got into:Where it started: My father, their grandfather, built companies my whole life, and he put me on the BCC of every email he ever sent so I could learn the business before I had a job in it. My actual first paycheck came from a summer carrying furniture up four story walk ups for a moving company in New York.The worst week of my career: one week in 2019 where we lost our biggest customer, our incoming CRO backed out the day before he was supposed to start, I found out I wasn't winning an award I really wanted, I tore my Achilles, and I missed a family trip to Israel, all in the span of five days.Firing people I liked: I've fired hundreds of people over 20 years, including good friends. My kids asked how I could do that, and we talked about why it's actually the kinder move when it's done right.The sacrifice question: I missed my son's first steps building BetterCloud, and I left the hospital right after my younger son was born to go straight to a VC meeting. My kids wanted to know if I'd still make that call today.Comparing myself to other CEOs: yes, I still get jealous scrolling LinkedIn. It was worse when I was actually running BetterCloud and too deep in the weeds to see anything but my own world.How I define success: the same answer my son got out of me at our first ever live show, the one that stumped Kass and Mike Lazarow in front of a packed room.This is a different kind of episode for the show, and it might be one of my favorites. Thanks for listening, and thanks to Sammy and Noah for the toughest interview I've ever done.Quote of the Show: "The way that I define success is being able to meaningfully impact other people's lives while significantly benefiting your own life." — David Politis, Host, Not Another CEO PodcastChapters:00:00:00 - Trailer 00:02:22 - BetterCloud's Biggest Lesson 00:04:52 - What Inspired Me to Want to Be a CEO 00:07:12 - My First Job 00:10:14 - Pitching BetterCloud to My Own Kids 00:15:21 - What 100+ Interviews Taught Me About Building a Company 00:20:31 - AI and the Skills That Won't Get Replaced 00:23:37 - The Hardest Days 00:29:35 - Still Bad At It, Jealous of Other CEOs 00:33:13 - How I Define Success 00:41:29 - The Sacrifice Question 00:46:47 - Trust Your Gut

Most founders assume the loneliness fades once the company succeeds.It doesn't. If anything, it gets quieter and harder to name.In this special compilation episode of Not Another CEO, David brings together lessons from nine founders, CEOs, and investors who have built, scaled, sold, and advised some of the most recognizable companies in tech.The conversation moves through why the seat is lonely in the first place, the false belief that you are the only one carrying it, and what the best CEOs actually build around themselves once they stop trying to carry it alone.Key Takeaways:Loneliness at the top isn't a personal failing, it's baked into the structure of the job: unpopular decisions, imperfect information, and a team that only ever sees half the picture.The belief that you are uniquely alone in your struggles is common and almost always wrong.Even the most people-first, culture-driven CEOs cannot fully escape the isolation of being the one who stays in the seat while everyone else eventually moves on.Founder loneliness is a default, not a fixed destiny. A co-founder, a coach, or a peer group can change the default entirely.The most effective support comes from someone with independent context on your business and your team.Support systems show up in real outcomes, not just in how someone feels.The founders who say they never felt the loneliness usually point to the same thing: a spouse, a family member, or a peer they could call and be fully honest with.Quote of the Episode"Your team has no conception of how lonely it is to be the CEO."— Adam Dell, Founder & CEO, Domain MoneyGuests Featured in This Episode:Marcus Ryu, Co-Founder & Former CEO, Guidewire — LinkedInAdam Dell, Founder & CEO, Domain Money — LinkedInChieh Huang, Co-Founder & Former CEO, Boxed — LinkedInNick Mehta, Co-Founder & Former CEO, Gainsight — LinkedInNadia Boujarwah, Co-Founder & Former CEO, Dia&Co — LinkedInChip Hazard, General Partner & Co-Founder, Flybridge — LinkedInKathryn Minshew, Co-Founder & Former CEO, The Muse — LinkedInMike Grossman, CEO (6x) & Author, Failure Is an Option — LinkedInKyle Porter, Founder & Board Chair, Salesloft — LinkedInChapters:00:00 – Trailer00:48 – Intro02:20 – Marcus Ryu03:34 – Adam Dell04:57 – Chieh Huang05:59 – Nick Mehta07:26 – Nadia Boujarwah08:43 – Chip Hazard10:10 – Kathryn Minshew12:34 – Mike Grossman15:38 – Kyle Porter16:38 – Closing Thoughts

Everything you think you know about why startups succeed might be wrongIn this episode, Mike Grossman, six-time CEO and mentor to first-time founders across Silicon Valley, breaks down what thirty years of running companies actually taught him.From the $200 million counteroffer that blew up his first company, to why he believes luck accounts for 80 to 90 percent of every outcome, Mike pulls back the curtain on what nobody tells you before you take the job. If you think success is mostly about hard work and good decisions, this conversation will make you rethink how you handle risk, pivots, and your own sense of control.Key Takeaways:Build a System to Find the Truth: Your direct reports won't always tell you what's really happening, whether they're afraid to or simply don't know themselves. Cut through the management chain and find the people who will tell you the truth.Hold Your Plans Loosely: A plan is obsolete the moment you make it. The goal isn't a perfect plan, it's a planning mindset flexible enough to adjust without losing the team.Stop Whiplashing Your Team: What feels like velocity to a founder can feel like chaos to everyone else. Pivot too often and even your own board will stop trusting your judgment.Beware Your Own Kool-Aid: Believing your company is destined for outsized value can cost you the deal in front of you. Mike turned down a $40 million offer and countered at $200 million. He got neither.Luck Runs the Table: Mike believes 80 to 90 percent of a company's outcome comes down to luck, not execution. Focus on what you can control and let go of the rest.Watch Out for the Debilitating Win: Founders who succeed once often can't understand why the second company isn't working the same way. It usually wasn't the formula. It was luck.Nobody Talks About the Loneliness: Nearly every first-time CEO Mike coaches struggles with anxiety and isolation, and most feel they can't show it to their own investors.Quote of the Show: Plans are useless because whatever plan you make is immediately out of date and you have to make adjustments to it. But if you don't make any plan and you just do it on a seat of the pants basis, everything is kind of ad hoc, you end up jerking the company around and people get frustrated.- Mike Grossman, Entrepreneur and AuthorConnect with Mike:LinkedIn: https://www.linkedin.com/in/migrossman/Book Failure is an Option: https://share.google/9DUEHB6596Eb1uXAaChapters:00:00 — Intro02:21 — The One Thing Mike Would Do Again At Every Company08:39 — Bill Campbell's Rule20:13 — Plans Are Useless, Planning Is Indispensable25:19 — The Pivot His Board Rejected26:58 — All Of Them Struggle With Their Mental Health30:47 — The $200 Million Deal He Blew Up38:58 — Luck Accounts For 80 To 90 Percent44:17 — The Debilitating Win54:16 — Remembering The Coach Of Silicon Valley

"You cannot outsource acquiring those first ten customers. You can't do it."In this episode of Not Another CEO, David breaks down the six tactical ways he's used, three separate times now, to land his first customers from zero. From holding a pizza party for international students to handing out fliers at the Atlanta airport taxi stand to asking his own uncle to buy a phone system, David gets specific about what actually works when you're starting from nothing.What's covered:-Why getting your first customers is harder now than ever, even though building product has never been easier-Reconnecting with former employers and coworkers who already trust you-How to actually use your investor network, even at the angel stage-Why showing up in person at trade shows and meetups still beats almost everything else-Building in public on social media, even when almost nobody engages at first-The one BCC email that got David a customer and an important hire at the same time-How to do cold outreach that people actually respond to-Why none of these six tactics scale, and why that's exactly the pointIf you're a founder still chasing your first ten customers, this one's for you.We cover more topics like this in full playbooks on our Substack. Subscribe to get the tactical deep dives, not just the highlights: notanotherceo.substack.comChapters:00:00 - Trailer00:44 - Why Finding Your First Customers Is Harder Than Ever05:20 - Tactic 1: Reconnect with Former Employers & Coworkers06:28 - Tactic 2: Tap Into Your Investor Network08:14 - Tactic 3: Show Up in Person (Trade Shows & Meetups)09:42 - Tactic 4: Build in Public on Social Media11:02 - Tactic 5: Tell Your Friends and Family12:02 - Tactic 6: Cold Outreach Done Right13:53 - Why Doing Things That Don't Scale Is the Entire Point