25 episodes

Extreme Uncertainty is a podcast about entrepreneurship. We interview founders from emerging tech ecosystems about what it's really like to launch a company. Founders share their lessons learned, their big wins, their crushing defeats, and the everyday struggles of running a startup.

Extreme Uncertainty Mike Leffer and Mike Ravenscroft

    • Business
    • 5.0 • 5 Ratings

Extreme Uncertainty is a podcast about entrepreneurship. We interview founders from emerging tech ecosystems about what it's really like to launch a company. Founders share their lessons learned, their big wins, their crushing defeats, and the everyday struggles of running a startup.

    Aaron Hsu - Catching the Tsunami

    Aaron Hsu - Catching the Tsunami

    What do you know about face masks?

    Chances are, you know a lot. We all do. What most of us don’t know is face masks present a real problem for medical professionals trying to communicate with people, particularly those who are deaf or hard of hearing. When Aaron Hsu and his cofounders launched ClearMask in 2017, it was the result of cofounder Allysa Dittmar’s experiences dealing with this issue firsthand. But what started as a part-time passion project in 2017 turned into something very different in 2020—a year when the world had a very real, very immediate need for masks.

    Aaron shares his journey over the last four years and how ClearMask went from filling dozens of orders each month to supplying hundreds of thousands of transparent face masks to hospitals and organizations all around the world. Aaron talks about the hurdles his team faced in launching a medical device company, the importance of preparing for success, how to deal with "champagne problems," and shares his advice for founders who suddenly find themselves with more business than they can handle. 

    We hope you enjoy this conversation with an inspiring founder. And we humbly dedicate this episode to all of our listeners who are on the front lines of the Covid crisis. We salute you and offer our sincere gratitude for all your dedication and sacrifice. 

    • 29 min
    Crossover Extremaganza - Mike & Mike on the Secure Ventures Podcast

    Crossover Extremaganza - Mike & Mike on the Secure Ventures Podcast

    And now, for something completely different. This week, Mike and Mike join Kyle McNulty on the Security Ventures Podcast. The Mikes had a wide-ranging conversation with Kyle about the challenges of raising capital as a cyber startup, how cyber venture fundraising differs from other verticals at the angel and seed stage, and what entrepreneurs should think about when they're prepping for a capital raise, and what can make a pitch really fly--or flop. We hope you enjoy the conversation, and check out the Secure Ventures podcast wherever you get your podcasts.

    • 1 hr
    The (Temporary) College Dropout

    The (Temporary) College Dropout

    What do you know about your employer-provided benefits?

    Chances are, not much. That's because benefits packages are complex and making an informed decision is challenging for employees. It's also a problem for insurance companies trying to underwrite policies, as well as employers seeking to give their employees the best option for themselves and their families.

    Akash Magoon is CTO and Co-Founder of Nayya, a platform providing personalized benefits education that's transforming the employee benefits industry. Akash shares his journey from (temporary) college dropout to CTO of a rapidly scaling technology startup. Akash grew up interested in healthcare and thought he'd become a doctor. But coming from a family of business owners, he also had an entrepreneurial streak. He dove into computer science at the University of Maryland and dropped out to found LIS Labs, a medical software startup. After exiting the company, doing a stint at AWS, and returning to finish his degree, Akash spent some time building software for insurance companies. It was then that he and his co-founder recognized the scope of the problems with employee benefits facing the industry, and they decided to do something about it.

    Akash gives his insights on what it takes to build a tech company, the challenges a CTO faces in trying to build scalable products, and his tips for those looking to get into the world of entrepreneurship. You can check out everything they're building at nayya.com.

    • 37 min
    Alex Bisignano - The Covid Pivot

    Alex Bisignano - The Covid Pivot

    What do you know about pivoting a tech company in the midst of a global pandemic?

    Unfortunately, if you're an entrepreneur, you know a whole lot about this very thing. For Alex Bisignano and his team at Phosphorous, 2020 started off strong. They had a growing business delivering next-generation sequencing (NGS) genetics testing products. And then Covid happened. After watching his run rate drop to near zero in the space of a few weeks, Alex, his team, and his investors worked together to engineer a company-wide pivot. Leveraging their collective expertise in testing, Phosphorous released a critical new product to market: at-home Covid tests. Phosphorous' saliva-based Covid tests are now available to individuals and organizations, and the company went from near failure to closing out 2020 with surging revenue and a critical new business line that's helping individuals and organizations fight the Covid pandemic. 

    Alex talks to the Mikes about the challenges the company faced this year, as well as his own personal pivot from financial services to medical technology startups. He shares his advice for entrepreneurs looking to get into the medtech space, his thoughts on what it takes to turn a tanker ship, and he tells us where the future of genetics testing is heading. You can check out what they're building at Phosphorous.com.

    • 41 min
    Cyndi Gula - Co-Founder for Life Part II

    Cyndi Gula - Co-Founder for Life Part II

    What do you know about Data Care?

    Our guest on the podcast today is Cyndi Gula, Co-Founder of Gula Tech Adventures and former VP of Operations and Co-Founder of Tenable Security. She’s also at the vanguard of a movement to change cybersecurity—everything from how we think about who “belongs” in the industry to the name itself. Cyndi started her career as a ceramics engineer before jumping with into a life of entrepreneurship. Since launching and exiting Network Security Wizards, Cyndi helped launch Tenable and scaled operations from 5 to over 500 employees. Cyndi tells us about her entrepreneurial journey and the challenges she faced scaling up a successful cybersecurity company. She gives her advice for those “silentpreneurs” who work behind the scenes, what it's like to go from founding companies to investing in founders, and her take on what needs to change to make cybersecurity a more inclusive environment for women and people of color.

    You can check out everything Cyndi and her Co-Founder for Life are building at the Gula Tech foundation at gula.tech, where you can also check out their brand new podcast, Gula Cyber Fiction, where she and Ron interview people from within and outside the cybersecurity industry—or should we say, the Data Care Industry.

    • 45 min
    Yanek Korff - Pay It Forward

    Yanek Korff - Pay It Forward

    What do you know about what keeps a Chief Information Security Officer up at night?

    Yanek Korff spent his career in cybersecurity as an engineer and business leader helping enterprises manage cybersecurity threats. It wasn't until he left FireEye and was considering his next move (in between playing a lot of XBox) that he and a former colleague were inspired to launch a company to help CISOs manage their cybersecurity operations. The inspiration? A tweet. (Seriously.) 

    Yanek shares his journey and the challenges of going from an engineer to a business leader to a cybersecurity co-founder and the lessons he learned along the way. He talks about the headaches facing CISOs, where the managed security services market is going, and his advice for founders. You can check out everything Yanek and his team are building at Expel.io and you can follow them @Expel_io.

    • 36 min

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