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Welcome to episode 302 of Trivia Time, the podcast quiz show! July Visual Round: https://tinyurl.com/5x82bz7p Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 301 of Trivia Time, the podcast quiz show! June Visual Round: https://tinyurl.com/mtmu3syd Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
In the latest episode of Founded & Funded, Madrona Partner Vivek Ramaswami sits down with Harley Sugarman, founder and CEO of Anagram, to unpack how one pivot, a flood of cold outreach, and relentless focus on behavior change transformed a niche tool into an enterprise platform serving companies like Disney and Pfizer. From landing enterprise logos off of nothing but wireframes, to outmaneuvering the 800-lb gorilla in a legacy industry — Harley's tactics are a masterclass for any founder trying to stand out in a crowded market. Transcript: https://www.madrona.com/how-anagram-landed-disney-with-cold-outbound-security-awareness-training Chapters: (00:00) Introduction (01:53) Harley Sugarman's Background and Journey (03:24) Founding Anagram (04:21) Initial Vision and Pivot (05:50) Challenges and Market Realities (06:54) Customer Feedback and New Direction (09:25) Executing a Startup Pivot (11:31) Cold Outreach Success (14:20) Security Awareness Training that works (18:52) Competing in a Crowded Market (24:48) Enterprise Sales Strategy (27:04) Fundraising Journey (28:54) Choosing the Right Investors (33:32) Advice for Founders (36:33) Future of Security Training
Welcome to episode 300 of Trivia Time, the podcast quiz show! June Visual Round: https://tinyurl.com/mtmu3syd Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 299 of Trivia Time, the podcast quiz show! June Visual Round: https://tinyurl.com/mtmu3syd Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Is the Darkglass Anagram really worth the hype? In this episode, Scott and Ian dive into the new analog multi-effects unit and pit it against the ever-popular HX Stomp. Could this be the gear that finally gets Scott to ditch his pedalboard for good? They break down the strengths of each, share their own setups, and ask the big question—which one's right for you?
Is the Darkglass Anagram really worth the hype? In this episode, Scott and Ian dive into the new analog multi-effects unit and pit it against the ever-popular HX Stomp. Could this be the gear that finally gets Scott to ditch his pedalboard for good? They break down the strengths of each, share their own setups, and ask the big question—which one's right for you?
Welcome to episode 298 of Trivia Time, the podcast quiz show! June Visual Round: https://tinyurl.com/mtmu3syd Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Anagram is pioneering a new approach to security awareness that treats employees as assets rather than liabilities. With $10 million in funding, the company is reimagining how organizations address their most significant security vulnerability: human error. In this episode of Category Visionaries, we spoke with Harley Sugarman, Founder and CEO of Anagram, about his journey from venture capitalist to founder and how he's challenging decades of ineffective security awareness training with a human-driven security platform that drives real behavior change. Topics Discussed: The fundamental problems with traditional security awareness training How AI is amplifying attackers' capabilities and the need for better human defenses Anagram's approach to personalized, puzzle-based, and in-the-moment security training The shift from treating humans as "risks to be mitigated" to valuable security assets Founder-led marketing strategies in the security industry Pivoting from security professional training to broader security awareness GTM Lessons For B2B Founders: Identify opportunities where market perception doesn't match reality: Harley noticed a massive gap between what CISOs considered their biggest vulnerability (human error) and how they addressed it (outdated, ineffective training). "If you ask 100 CISOs where an attack will come from, 90-95 will say one of their people will click on a phishing link," yet solutions remained antiquated. This disconnect signaled an opportunity to create a truly differentiated product. B2B founders should look for areas where customer actions don't align with their stated priorities, as these represent prime opportunities for innovation. Frame your solution to break industry paradigms: Rather than accepting the industry framing of "human risk management," Harley positioned Anagram around "human-driven security" — shifting from seeing employees as liabilities to valuable assets. "I hate that framing so much because it puts the onus on the human," he explained. "What I have been trying to frame our company around is this idea of human-driven security, which is taking humans and making them a line of defense." This reframing helps differentiate Anagram from competitors and resonates more positively with both security leaders and end users. Use data to overcome status quo inertia: In industries with deeply entrenched practices, the biggest challenge is often skepticism about whether a new approach can actually work. Harley's solution? Let the data make the case. "For us, we are very insistent on looking at the data showing customers, 'Hey, before you introduced us, this is the number of incidents you were seeing. After you introduced us, this is the number of incidents you're seeing.' And I think that's ultimately the thing that changes minds." Data-driven results help overcome the "it's always been this way" mindset that can derail innovative B2B solutions. Employ a land-and-expand strategy for complex purchases: Anagram uses a methodical approach to win over skeptical buyers: "We very much take a land and expand strategy where we'll go in, augment a specific part of the program, show them that this is actually making a meaningful difference in the data, and then that becomes a very easy business case." For B2B founders selling complex or paradigm-shifting solutions, demonstrating tangible value in a limited implementation can pave the way for broader adoption throughout the organization. Don't dismiss "old school" outreach tactics: Despite the emphasis on modern marketing techniques, Harley found success with traditional outbound methods: "So far, it has been pretty much exclusively outbound. So emails, LinkedIn, cold calling...which still works, by the way. I was shocked." B2B founders, particularly those targeting enterprise customers outside the tech bubble, should remember that traditional outreach methods can still be highly effective even when they seem outdated in startup circles. Embrace personal branding with authenticity: After initially feeling uncomfortable with founder-led marketing, Harley found success by finding an authentic voice while taking inspiration from founders like PostHog's James Hawkins. "It does feel cringy. I hate most social media things... It was very much an intentional decision to step out of my comfort zone." By focusing on engagement metrics rather than personal comfort, Harley discovered that his personal content consistently outperformed company posts. B2B founders should measure the results of their personal branding efforts rather than judging them solely on comfort level. Know when to pivot quickly: Perhaps Harley's most critical decision was recognizing when their initial product wasn't gaining traction and pivoting decisively: "The biggest decision that we made was pivoting... I'm really proud of the fact that we very quickly made the decision to basically throw away all this work that we had done and move into this more general purpose awareness tool." B2B founders should be willing to abandon their original vision when market signals indicate a better opportunity, even if it means discarding substantial work. // Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co // Don't Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM
Welcome to episode 297 of Trivia Time, the podcast quiz show! June Visual Round: https://tinyurl.com/mtmu3syd Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 296 of Trivia Time, the podcast quiz show! May Visual Round: https://shorturl.at/uVThi Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 295 of Trivia Time, the podcast quiz show! May Visual Round: https://shorturl.at/uVThi Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 293 of Trivia Time, the podcast quiz show! May Visual Round: https://shorturl.at/uVThi Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 293 of Trivia Time, the podcast quiz show! April Visual Round: https://shorturl.at/vVa0D Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 292 of Trivia Time, the podcast quiz show! April Visual Round: https://shorturl.at/vVa0D Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 291 of Trivia Time, the podcast quiz show! April Visual Round: https://shorturl.at/vVa0D Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 290 of Trivia Time, the podcast quiz show! April Visual Round: https://shorturl.at/vVa0DWebsite: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 289 of Trivia Time, the podcast quiz show! April Visual Round: https://shorturl.at/vVa0DCheck out Photosynthesis: https://www.photosynthesisolympia.com/ Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 288 of Trivia Time, the podcast quiz show! March Visual Round: https://shorturl.at/s8vbW Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 287 of Trivia Time, the podcast quiz show! March Visual Round: https://shorturl.at/s8vbW Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 286 of Trivia Time, the podcast quiz show! March Visual Round: https://shorturl.at/s8vbW Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 285 of Trivia Time, the podcast quiz show! March Visual Round: https://shorturl.at/s8vbW Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Dr. Grisma Shah's debut novel Anagram Destiny is a soul warming love story nestled in an inspiring tale of the American dream, manifesting an Indian immigrant success story shattered by the evils of globalization– paying homage to a generation of immigrants who held their heads low so one day, their children could lift theirs high. To learn more about Dr. Shah and her novel go to www.shahgrisma.com.
Welcome to episode 284 of Trivia Time, the podcast quiz show! February Visual Round: https://shorturl.at/vI4C9 Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Despite employers requiring their employees to complete yearly cybersecurity training courses, human-driven cybersecurity breaches still happen. The problem could even get substantially worse as generative AI increases the scale and personalization of social engineering campaigns. Learn more about your ad choices. Visit podcastchoices.com/adchoices
Thousands of exposed GitHub repositories, now private, can still be accessed through Copilot Cellebrite halts product use in Serbia following Amnesty surveillance report New Ghostwriter campaign targets Ukrainian Government and opposition activists in Belarus Huge thanks to our sponsor, Conveyor It's 2025. This is your second sign to get a trust center if you don't already have one. Reduce manual work by 80% when you can share one link to your trust center and let customers download what they need on demand. Trusted by the world's top B2B companies, Conveyor's enterprise-grade trust center is specially designed to handle multiple products, complex orgs, and with AI first so you can even push your customers to self-serve their own AI answers to questionnaires. Learn more at www.conveyor.com.
Welcome to episode 283 of Trivia Time, the podcast quiz show! February Visual Round: https://shorturl.at/vI4C9 Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
I love any time a manufacturer comes on the show to share some insight into what they have planned to help our industry! This episode was recorded live at Fulcrum 2025, and we hear about the new products, new people and new things happening with Anagram! My ears definitely perked up when they mentioned the number of new foil designs and new formats they have coming for us this year… but we'll also get to hear more about their launch into latex. Learn about what “better together” means for them; how many latex colors are on the way; how they perform with helium, Hi-Float and Hi-Shine; and the size range. Then we wrap up by talking about the kinds of opportunities balloon decorators have with the closing of Party City. Anagram is investing in everything from innovation, to engineering, to industry education and their confidence in their quality is well deserved. And in the UGlu Hotline, hear a tip for getting yourself some video content for social media. RESOURCES MENTIONED: Presenting sponsor: 17hats (get 50% off your 1st year) Anagram Other sponsors & resources: Havin' A Party Wholesale (save 5% on orders $200+ with code PODCAST) Courtney Lynette Creative Co 2025 Bright Balloon Business Planner UGlu by Pro Tapes (save 5% on orders $200+ at Havin' A Party with code PODCAST) Call into the UGlu Hotline to ask a question or leave advice! (262) 221-8514 Balloon Boss Mastermind & Summit - - - - Get bonus episodes 50 Ideas for Email Marketing | Join the Bright Balloon email list Freeform Freedom | More courses @thebrightballoon The Bright Balloon on YouTube
Welcome to episode 282 of Trivia Time, the podcast quiz show! February Visual Round: https://shorturl.at/vI4C9CA Wildfire Fundraiser: https://gofund.me/8ff696f1Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 281 of Trivia Time, the podcast quiz show! February Visual Round: https://shorturl.at/vI4C9CA Wildfire Fundraiser: https://gofund.me/8ff696f1Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 280 of Trivia Time, the podcast quiz show! February Visual Round: https://shorturl.at/vI4C9CA Wildfire Fundraiser: https://gofund.me/8ff696f1Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.comWebsite: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 279 of Trivia Time, the podcast quiz show! January Visual Round: https://tinyurl.com/2p9z622hCA Wildfire Fundraiser: https://gofund.me/8ff696f1Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 278 of Trivia Time, the podcast quiz show! January Visual Round: https://tinyurl.com/2p9z622h Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 277 of Trivia Time, the podcast quiz show! January Visual Round: https://tinyurl.com/2p9z622h Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 276 of Trivia Time, the podcast quiz show! January Visual Round: https://tinyurl.com/2p9z622h Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 275 of Trivia Time, the podcast quiz show! December Visual Round: https://tinyurl.com/2uahskcp Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 274 of Trivia Time, the podcast quiz show! December Visual Round: https://tinyurl.com/2uahskcp Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 273 of Trivia Time, the podcast quiz show! December Visual Round: https://tinyurl.com/2uahskcp Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 272 of Trivia Time, the podcast quiz show! December Visual Round: https://tinyurl.com/2uahskcp Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 271 of Trivia Time, the podcast quiz show! November Visual Round: https://shorturl.at/3bUHe Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 270 of Trivia Time, the podcast quiz show! November Visual Round: https://shorturl.at/3bUHe Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 269 of Trivia Time, the podcast quiz show! November Visual Round: https://shorturl.at/3bUHe Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 268 of Trivia Time, the podcast quiz show! November Visual Round: https://shorturl.at/3bUHe Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to a special bonus episode of Trivia Time! November Visual Round: https://shorturl.at/3bUHe Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 267 of Trivia Time, the podcast quiz show! October Visual Round: https://shorturl.at/GZGEt Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 266 of Trivia Time, the podcast quiz show! October Visual Round: https://shorturl.at/GZGEt Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 265 of Trivia Time, the podcast quiz show! October Visual Round: https://shorturl.at/GZGEt Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 264 of Trivia Time, the podcast quiz show! October Visual Round: https://shorturl.at/GZGEt Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 263 of Trivia Time, the podcast quiz show! October Visual Round: https://shorturl.at/GZGEt Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com
Welcome to episode 262 of Trivia Time, the podcast quiz show! It's our five year anniversary!September Visual Round: https://shorturl.at/BVo8b Website: https://triviatimepodcast.comEmail: triviatimepodcast@gmail.com