Skip to main content
Extreme Uncertainty

Extreme Uncertainty

By Mike Leffer and Mike Ravenscroft
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.
Where to listen
Apple Podcasts Logo

Apple Podcasts

Google Podcasts Logo

Google Podcasts

Overcast Logo


Pocket Casts Logo

Pocket Casts

RadioPublic Logo


Spotify Logo


Currently playing episode

Samier Mansur - Mission Driven

Extreme Uncertainty

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. 
April 22, 2021
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.
April 01, 2021
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
March 18, 2021
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
March 05, 2021
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, 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.
February 18, 2021
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 and you can follow them @Expel_io.
February 12, 2021
Ellison Anne Williams - The Holy Grail
What do you know about cryptography? For decades, researchers and data scientists in the federal government and commercial enterprises have invested millions to crack the code on homomorphic encryption—that is, how to keep data secure while it's in use. Our guest on the podcast today spent the first part of her career at the National Security Agency as one of those scientists, and she's the one who cracked the code.  In 2016, Dr. Ellison Anne Williams left the NSA to found Enveil, the first commercial company to provide security for data in use. Also known as the “Holy Grail” of cryptography, Enveil's homomorphic encryption platform is a technical breakthrough and represents a fundamental leap forward from traditional privacy and security technologies. Though Ellison Anne spent her early career "collecting degrees" in math and machine learning before joining the Johns Hopkins Applied Physics Lab and eventually the NSA, she recounts how for much of her time in government she felt like a fish on a bicycle--an entrepreneur working in a massive government bureaucracy. Ellison Anne recounts her entrepreneurial beginnings running a cake business in high school, and talks about a career in government that was undergirded by a desire to work on entrepreneurial endeavors. Since founding Enveil, Ellison Anne discovered that what she learned about working the gears in a government bureaucracy helped her prepare for navigating enterprise sales cycles. She shares her advice for founders and gives us a look at what the market for privacy and data security will look like in 5-10 years time. You can check out their groundbreaking work at and you can follow them @enveil_inc.
January 28, 2021
Ron Gula - Co-Founder for Life
What do you know about launching, scaling, and exiting a cybersecurity startup? Our guest today needs no introduction. Ron Gula is the Former CEO and Co-Founder of Tenable, a global cybersecurity company headquartered in Columbia, MD. Ron and his wife Cyndi launched Tenable in 2002 and saw it through to a successful IPO in 2018. Over that time, Ron and Cyndi emerged as leading voices in cybersecurity through their work as investors, though-leaders, and philanthropists. In addition, Ron and Cyndi have invested in dozens of cybersecurity startups, many of which have scaled and come to define the startup ecosystem in the Mid-Atlantic.  Ron talks about starting out in the Air force and his journey from serving his country in cyber defense for the NSA to launching an industry-leading cybersecurity company. We discuss his post-IPO move into angel and venture investing with his wife and co-founder for life Cyndi, and he shares his advice for founders looking to launch and scale a new venture.  You can check out Ron and Cyndi's new adventures in tech at, and you can find Ron on LinkedIn. 
January 21, 2021
Peter Baumann - The Dangerous Gene
What do you know about data discovery? Organizations large and small struggle to manage and make use of their data. Whereas most organizations understand their structured data assets,  unstructured data poses a security risk for those companies that don't manage and secure it. It's also a potential treasure trove of insights that most companies aren't equipped to tap into. ActiveNav helps organizations discover and manage their unstructured data to make use of their data assets and minimize risk of breach and ensure proper data governance. CEO and Founder Peter Baumann launched ActiveNav in 2008 just as the issue of data in the wild started to come into the conversation, and over the last ten years he and his team have scaled the company into a key player in the data discovery market. But Peter's entrepreneurial journey didn't start with data analytics. We talk with Peter about his entrepreneurial origins making and selling wine to pay his way through college, the challenges of building and scaling a data company, moving a company's operations overseas, and his take on how entrepreneurs can overcome the "maturity bias" as a technology firm raising venture capital. 
January 14, 2021
Samier Mansur - Mission Driven
What do you know about launching a non-profit technology venture? Our guest on the podcast today is Samier Mansur, CEO and Founder of No Limit Generation, a Washington DC based non-profit that equips refugee aid-workers with trauma informed mental health and wellness tools developed by world renowned experts. While working to support on the ground relief efforts during the Rohingya refugee crisis, Samier realized that traditional aid workers were not equipped to address the mental health needs of children in crisis zones. Having previously co-founded the successful public safety technology company LifeSafe, Samier realized this might be a problem that technology could help solve.  On the podcast, Samier shares his journey from international relations major to tech founder to the world of non-profits. He gives his advice for founders looking to launch a mission-driven enterprise, how to cope with the challenges of being an entrepreneur, and how we can use technology and entrepreneurship to build a better world. You can check out all the work Samier and his team are doing at and follow them @nolimitgen.
December 17, 2020
Chandler Givens - Timing the Market
What do you know about device fingerprinting? When Chandler Givens and his co-founder launched TrackOff, the market for protecting privacy on the internet was taking off in a big way. As Chandler learned quickly, there's nothing like learning to surf in rough seas. Chandler talks about TrackOff's humble beginnings and subsequent growth, their punk-rock marketing tactics that garnered national media coverage, and their eventual acquisition by global cybersecurity firm Avast. He shares the challenges of scaling a startup and offers his advice to founders who are going through the grind and asking themselves, "When is the right time to exit?" Since the acquisition of TrackOff, Chandler has taken over as Director of Product Management for Consumer Privacy at Avast, and he talks about how integrating his company's product and team into the company has helped them continue to work toward identity protection at scale. 
December 10, 2020
Ken Malone - Extreme Certainty
What do you know about aquaculture? Or machine vision? How about drug design? Custom materials? It's a lot of ground to cover. Thankfully, our guest on the podcast this week is the perfect trail guide. Ken Malone is the Co-Founder of Early Charm Ventures, a Baltimore-based venture studio that turns science into business. Ken spent most of his career as an engineer-turned-entrepreneur, identifying promising technologies at the university research stage and accelerating them into the market. After over a decade in the private sector and academia, Ken and his wife decided there was an opportunity in Baltimore to take early stage innovations and turn them into profitable businesses. In a world where venture capital and market-making have an outsize role in technology startups, Early Charm takes a different approach: taking good ideas and building a sustainable businesses around them. Ken shares his stories of coming up in the corporate world, how his interest in working with smart people on groundbreaking research led to founding a venture studio, and his advice for founders. You can learn more about the new ventures they're building at And, in the words of Ken Malone: Embrace the certainty.
December 02, 2020
Ishan Girdhar - Smart Money
What do you know about third party vendor risk assessment? Our guest on the pod today is Ishan Girdhar, CEO and Founder of Privva. Privva is an Arlington-based provider of third-party risk assessment tools for enterprises. Ishan shares his story of jumping into the world of entrepreneurship after pitching the idea for Privva in meetings with C-Suite executives and realizing he could sell the solution with just a pitch deck. From identifying the opportunity to actually launching the business, Ishan talks about the challenges they faced hiring top talent, the allure of sales efforts that end up being whale chases, and what he'd do differently if he could start over (note to founders everywhere: invest in marketing early.) You can check out everything Ishan and his team are building at and follow them on Twitter @PrivvaInc.
November 19, 2020
Jess Gartner - Agent of Change
What do you know about managing school district budgets? This week, the Mikes speak with Jess Gartner, CEO and Founder of Allovue. Allovue is a Baltimore-based Ed-Fintech company that helps school districts allocate resources and manage their budgets to ensure equitable access to education resources for all students.  Jess started her career as a teacher in Baltimore City Schools. In that time, she came to experience the harsh realities facing schools and students--everything from a profound lack of resources to an unequal distribution of opportunities. Jess decided to leave teaching and build a solution that could start to help school districts solve some of the challenges managing their finances to serve their students more effectively. We talk to Jess about how she found her footing as a first-time CEO and how the skills she built in the classroom translated into her role as a founder and a corporate leader. We also talk about the challenges facing women in tech and in particular female CEOs trying to raise capital. Jess gives her advice to founders and reminds us that it's up to all of us in the tech community to work to help level the playing field for entrepreneurs from diverse backgrounds. 
November 12, 2020
Marcus Bullock - Build the Parachute on the Way Down
What do you know about communicating with an incarcerated loved one? For millions of Americans, this problem is all too familiar. And it’s a problem our guest on the podcast today experienced firsthand. Marcus Bullock is the CEO and Founder of Flikshop, a company that helps people communicate and maintain connections with their incarcerated friends and family members. Marcus shares his personal journey from being incarcerated at the age of 15 to founding a company that has grown to serve people at over 2500 prisons nationwide. He offers his advice to founders on everything from building a network to raising capital to executing on your vision. It's the kind of story you don't often hear in the world of tech, and one we hope you enjoy.  FlikShop has been featured in the Washington Post, Forbes, CNN, NPR, and dozens of other national media outlets. Marcus has given TED Talks, he was selected as one of The Roots’ 2019 100 Most Influential African Americans in the US, he is a member of the Justice Policy Institute’s Board of Directors, Advisory Board Member of Princeton University’s Prison Teaching Initiative, and is an Advisor to the Aspen Institute’s Opportunity Youth Incentive Fund. You can check out the important work Marcus and his team are doing at and you can follow them on Twitter and on Instagram @flikshop.
October 29, 2020
Grant Elliott - Just Keep Swimming
What do you know about cybersecurity in healthcare? You’ve probably heard news reports about the surge in cybersecurity incidents across the healthcare industry throughout 2020. The reality is that developing and maintaining a robust cybersecurity and risk management program is a challenge for any organization. For healthcare companies in particular, it’s difficult to stay up to date with a rapidly evolving cybersecurity compliance landscape. Our guest on the pod today saw these problems firsthand when he was CISO at the health IT company Voxiva and he decided to do something about it. Grant Elliott is CEO and Founder of Ostendio. Grant tells the story of how he realized there was a market opportunity in healthcare security and compliance, and how he made the leap from the steady ride of the corporate C-suite to the extremely uncertain world of tech entrepreneurship. Grant gives his advice for founders (“Just don’t do it”) and shares his secret for successfully scaling a technology company (TLDR: It’s the title to this episode.) Grant teaches courses on business and entrepreneurship at the Pratt Institute, he is the Founder and Former President of the Healthcare Cloud Coalition, and in his spare time he mentors and advises entrepreneurs.  You can check out all the healthcare compliance and risk management tools Grant and his team are building at and you can follow them on Twitter @Ostendio.
October 22, 2020
Colin Dunn - The Harley Davidson Purchase
What do you know about our nation’s critical infrastructure? Enough to concern you? Us too. That’s why we called up Colin Dunn, CEO of Fend Technologies, who reminded us just how scared we should be--and what his startup is doing to try to help us all sleep easier at night.  Colin is an engineer by training, and he spent the early part of his career working with governments and utilities on many of the challenges that persist in the industry. Colin saw how critical sites across the country were struggling to optimize energy usage, maintain aging assets, and protect critical systems from cyber attack. After his MBA and a few years in the private sector, Colin made the leap into the world of entrepreneurship--a move he likens to "finally buying that Harley Davidson." Colin shares the challenges of launching a hardware business, and how his team decided not to pursue venture capital and instead funded the company's early growth with SBIR grants, Virginia CRCF grants, and government contracts. Colin talks about the importance of believing in the mission of your company and setting out to solve problems that need to be solved. Which, we think, is spoken like a true engineer. You can check out everything they're building to keep our critical infrastructure safe at
October 15, 2020
Liza Rodewald - Accidental Entrepreneur
What do you know about remote work? Yep. Us too. We all know pretty much everything there is to know about remote work. Nothing more to learn here. But here's another question: What do you know about being a military spouse? Our guest on the podcast today is Liza Rodewald, CEO of Instant Teams. Liza is a military spouse who moved frequently with her family. She's also an accomplished software engineer who ran her own business for over a decade building custom enterprise applications for government and commercial clients. Liza and her cofounder realized there were millions of military spouses around the world just like them who were highly skilled and well qualified to work on distributed teams. And when they learned there were thousands of businesses that needed help scaling remote teams for customer support and operations, they realized they were onto something big. Liza shares her journey as an "accidental entrepreneur," and explains how she went from running her own technology consulting business to launching a venture-backed tech company. Liza shares her perspective on building a fully remote business, learning to manage a growing team, and raising venture capital. You can learn all about how Liza and her team are helping military spouses the world over find fulfilling work at, and you can follow them on Twitter @Instant_Teams.
October 08, 2020
Gideon Taub - Building Momentum
What do you know about charitable giving? About 80% of all charitable donations in the US come from individuals, which in 2019 was over $300 billion. However, most charitable giving is ad hoc and many people struggle to effectively manage their donations. For corporations and banks seeking to incentivize charitable giving with donor-match programs, that challenge is even greater.  Our guest on the podcast today is Gideon Taub, CEO of Pinkaloo Technologies. Gideon and his team experienced these problems firsthand and launched Pinkaloo to modernize charitable giving for individuals, corporations, and banks. Since launching in 2017, Pinkaloo has grown to serve banks and corporations across the country, and the team has received accolades from industry as a company at the forefront of the modern giving movement. Gideon talks about how his experience at another high-growth startup, Videology, helped him develop the skills he needed to launch his own venture, and he tells us about the challenges his team faced trying to sell a fintech solution to corporations and banks. Gideon shares his advice for founders about how to build momentum for a new venture by focusing on go to market fundamentals and being open to learning and adapting as your company grows. You can check out all the solutions Gideon and his team are building to help modernize charitable giving at and you can follow them on Twitter @Pinkalootech.
October 01, 2020
Mark Olcott - Not Within These Four Walls
What do you know about veterinary medicine? It’s alright—neither did we before we spoke with Mark Olcott, CEO of Vitus Vet. Turns out it takes a vet to understand there are challenges to running a veterinary practice beyond caring for sick animals. In an industry that still relies on fax machines to send medical records, veterinary practice owners struggle to manage payments, schedule appointments, and streamline back office workflows. Mark saw the problem firsthand when he was a vet managing his own practice, and he tells the story of Vitus Vet's origins when he met his co-founder Kalpesh Raval at the University of Maryland Robert H. Smith School of Business. Mark and Kalpesh took an idea they developed in one of their MBA courses and built a prototype, did extensive customer discovery, and laid the groundwork for their go-to-market strategy--and then pivoted the company soon after. Mark shares some of the lessons he has learned as a lifelong entrepreneur, from his first venture selling candy at the bus stop when he was twelve, all the way through to building a corporate culture at Vitus Vet. You can check out all the tools Vitus Vet is building to make the lives of vets and pet owners easier (and, of course, keeping those puppies and kittens happy and healthy) at, and you can follow them on Twitter @VitusVet.
September 24, 2020
Nick Culbertson - Don't Make Excuses
What do you know about drug diversion? Our guest today is Nick Culbertson, CEO and Co-Founder of Protenus, a Baltimore-based healthcare technology company. Nick was in medical school and doing research at Johns Hopkins University when he and his eventual Co-Founder realized that hospitals have a big problem managing risk and maintaining compliance--a problem their work in data analytics might be able to solve. Nick talks to us about how his background as a Green Beret in the US Army prepared him to step into the role of a founder, and how Protenus went from a two person startup to a company with over 100 employees serving healthcare systems across the country. We talk about the leadership team's response to the call to action of the Black Lives Matter movement, and we discuss how Nick and his team have built a culture of inclusion at Protenus. Nick also offers his advice for entrepreneurs who are working to launch a venture, and gives us his perspective on how strong mentors are an entrepreneur's most valuable asset. Protenus was recognized in Forbes as a 2020 “Best Startup Employer” and a “Cool Vendor” in Artificial Intelligence by Gartner. Protenus received the 2019 Innovation of the Year in Data Security award by Healthcare Informatics and was recognized as one of the Best Places to Work by Modern Healthcare in 2018, 2019, and 2020. Protenus completed its Series C financing in August 2019, and is one of Baltimore's leading employers in healthcare analytics. Nick Culbertson is also a finalist for Ernst & Young's "Entrepreneur of the Year 2020" Award. You can check out all the AI-driven healthcare tech Nick and his team are building at, and you can follow them on Twitter @Protenus.
September 17, 2020
Craig Stevenson and Jessica Crytzer - Dump Trucks Full of Money
What do you know about cloud computing environment visualization? For episode three, we spoke with startup warriors Craig Stevenson, CEO, and Jessica Crytzer, Chief Revenue Officer of HyperQube Technologies. HyperQube is a platform that makes visualizing entire cloud networks as simple as clicking a button—but how the team got there wasn’t so simple. Craig talks about his early days as an engineer at Raytheon training cybersecurity teams and how he waited years to take the leap into entrepreneurship, working alongside startups and mentoring cybersecurity entrepreneurs before becoming one himself. He and Jessica share their lessons learned about how to build a high growth technology business, as well as the challenges of raising capital and pulling together a world class team. And we get an inside look at how they pivoted the company when they discovered a problem that was much bigger than the one they originally set out to solve. You can check out all the game-changing cloud visualization tools Craig and Jessica are building at, and you can follow them on Twitter @HyperQubeTech.
September 10, 2020
Matt Bjonerud - The Fog of War
What do you know about the challenges of raising debt capital to finance the growth of a mid-market company? In this episode, we spoke with Matt Bjonerud, CEO of Cerebro Capital, a Baltimore-based fintech startup. Matt spent the early part of his career in corporate banking with PNC, where he learned about the challenges mid-market companies face raising capital, as well as the challenges prospective lenders face in finding lending opportunities to the mid-market. Matt launched Cerebro Capital to simplify an opaque process that was ultimately hampering corporate growth for mid-market companies globally. In our conversation, we talk about Matt's early days as an entrepreneur and how his team got the company off the ground, and we discuss the strategies his team used to close the company's venture round just as COVID-19 began to hit. Matt also offers his perspectives on how startups can answer the call to action of the Black Lives Matter movement. Matt reveals the steps his team took to rethink their entire hiring process and how he overcame his own cognitive biases to build a more diverse team. You can check out all the innovative fintech products Matt and his team are building at and you can follow them on Twitter @cerebrocapital. 
September 03, 2020
Joe Saunders - Logically Unique
What do you know about software hardening? For our first episode, we sat down with Joe Saunders, CEO of RunSafe Security, a cybersecurity company based in Tysons Corner, Virginia. Joe is the Founder and CEO of RunSafe, and he built his career in tech as part of the Management Team at TARGUSinfo, where he helped grow the company to over $100M in revenue. Joe serves on the advisory boards of numerous tech companies and is an expert in cybersecurity and enterprise sales strategy. He talks to us about how RunSafe is building innovative cybersecurity solutions to protect enterprises, and about the challenges of bringing a cybersecurity product to market. We also get a firsthand look at "The School of Hard Knocks," a bounty of lessons Joe learned from his career in entrepreneurship. He's also a Michigan Wolverine, which, although we don't talk about it on the podcast, might be his crowning achievement. Check out everything Joe and his team are building at and follow them on Twitter @RunSafeSecurity.
August 24, 2020
Minimum Viable Product
Welcome to Extreme Uncertainty, a podcast about entrepreneurship. In this teaser episode, we give thanks to our early adopters, and explain why we're making this podcast. 
August 24, 2020