
DESIGNING SUCCESSFUL STARTUPS
A weekly podcast focused on founders (and the people who support them) who are my guests and their lessons learned and plans for success. Join me, and a special guest for each episode. New episodes drop every Wednesday.
Professor-turned-entrepreneur, and founder of nine companies two of which had strong exits, Jothy Rosenberg talks with business leaders and personal achievers. “Designing Successful Startups” explores the challenges and rewards of entrepreneurship, overcoming adversity, and where grit and perseverance can get you. Be inspired by others, and push yourself along your path to success and fulfillment.
JOTHY ROSENBERG
JOTHY’S STORY
In two episodes, Jothy talks about his source of grit and then about all things related to Who Says I Can’t including his memoir, a TV Series, the non-profit foundation, his TEDx talk, Adventures on the Can Do Trail children’s book, his new book “Tech Startup Toolkit”, and this podcast.
Listen to or watch both episodes from here. 🎧
Recent Episodes
Jothy Rosenberg interviews Pablo Martell, a CPA and fractional CFO who helps startups navigate critical tax and financial decisions. Pablo emphasizes the importance of proper entity structure from day one, explaining how C-corp formation enables future fundraising while preserving QSBS tax benefits. He details crucial concepts like 83(b) elections for equity grants, R&D tax credits that can offset payroll taxes even when unprofitable, and the need for ongoing compliance with evolving tax requirements. As a fractional CFO, Pablo helps founders understand cash burn, runway calculations, and financial modeling for fundraising while ensuring they don't make costly tax mistakes early on.Retry
Jothy Rosenberg interviews Andrew Skafel, founder and CEO of Edgewater Wireless, a fabless semiconductor company solving WiFi's fundamental limitation. Their "spectrum slicing" technology creates multiple concurrent channels from a single WiFi device, like turning a single-lane road into a multi-lane highway. Initially targeting stadiums, they pivoted to homes and enterprises after Cable Labs showed them the broader market opportunity. Their AI-powered solution proactively manages spectrum allocation and works with existing devices. Recently awarded a major Canadian government grant, Edgewater has validated their technology through massive scale testing of 6 million devices across 750,000 homes with Liberty Global.Retry
Jothy Rosenberg interviews Aryan Mohindra, a 20-year-old entrepreneur who transformed his life at age 12 after failing school and being 40 pounds overweight. Inspired by a quote from a TV show ("you don't know what you're fighting for"), Aryan discovered the power of having compelling reasons behind actions. He turned his grades around, lost 70 pounds, started networking in real estate at 15, landed internships, gave a TEDx talk, and now runs a podcast interviewing executives plus a fitness consulting business. His core message: challenging perceived requirements and finding your "reason worth fighting for" unlocks paths others miss.
Jothy Rosenberg interviews Sean Broderick, a serial entrepreneur turned VC who went from coding in high school to running Techstars Boston and now investing at D Lab. Sean challenges conventional wisdom by arguing that investors don't back ideas—they back founders. He emphasizes that integrity, intelligence, and grit matter more than brilliant concepts, noting "some of you are here in spite of your idea." Sean shares how the best startups often emerge during economic downturns, discusses his journey from multiple failed companies to successful exits, and explains why he believes failure is a better teacher than success for entrepreneurs.
Jothy Rosenberg interviews Andy Levine, founder of DuVine Cycling + Adventure Company, who started leading bike tours in France's Burgundy region in 1992 straight out of college. Andy built a boutique luxury cycling company over 30 years, maintaining small group sizes (maximum 14 people) while scaling to 200+ employees globally. He emphasizes authentic local connections, exceptional hospitality, and staying true to core values rather than expanding everywhere. Andy shares how company culture became his competitive advantage, the challenges of the travel industry including COVID-19's near-fatal impact, and how his grit comes from not wanting to disappoint customers and team members.
Jothy Rosenberg interviews Ali Madhavji, a Vancouver-born entrepreneur now based in Singapore who went from refugee parents and a $1.50/hour paper route to building a successful crypto exchange and becoming a Web3 investor with 200 companies in his portfolio. Ali shares his journey from startup founder to creating Blockchain Founders Fund, explaining how blockchain technology can solve multi-party trust issues and help billions of unbanked people access financial services. He discusses his investment criteria focusing on team track record and execution speed, common founder mistakes around alignment and customer discovery, and his vision for blockchain's mainstream adoption in solving real-world problems.
I am ADHD and I believe that it is actually my secret weapon. My ADHD has been responsible for all of the success I've had over my professional life. As a kid it was tough - constantly being told 'you're being disruptive, sit down, you're disrupting the class.' I've been told that I was broken by every single teacher so many times that there was no possible way I could actually be doing something good. But it turned out to be an incredible advantage. I've always lived by one simple rule: you can get everything you want simply by offering help first.
I grew up working for my dad, cleaning office buildings when I was too young to drive. Then I moved to Wall Street and they basically said we're gonna take an entire class of people and not do business with them because they're not rich enough. That struck me as odd. I was involved in investment banking during the dot-com run up, and I'd be looking at prospectuses knowing this company was garbage, but it didn't matter because it was sellable. That bothered me. It didn't jive with my moral compass, so we said let's go do our own thing.
As an immigrant woman coming on dependent visa with no work permit, I had no clue what I was going to do in America. When I interviewed for minimum wage jobs and told them I wanted to launch my own business, nobody offered me the job. That's when I realized I was ready. I started with free lessons in a church basement, serving 400 students that first summer. Now, three years later, we have three centers in Silicon Valley serving over 1,000 students annually. Self-doubting is normal, but just be confident and give it a try.
One thing that I've done is doing it all by myself and not putting the work marketing early on. What I mean by this is all of us have phones and Internet and just recording the process, getting on social media, sharing the process. Either it's talking about your business, talking about the services that you do, ensuring with the world how we serving you, what works, what doesn't work and not being scared of it. I've realized that I kind of done a lot of things backstage, but not really package them well into case studies and convert these into content.
There's a difference between temporary and total failure. Total failure is when you walk away from the process, because now you are not utilizing the experience and the setbacks to your advantage. But if you fail and everything went wrong, you fell off the horse and you beat yourself up, but next day you get back on it—that's not failure. That is far from it because you're still in the process. As long as you stick to it, those eventually become the best lessons, the foundation of progress. You don't call it failure. You call it a process.
One of the most important things that some new podcasters get wrong is not allowing enough time to see the true potential of a podcast, especially when you have a pretty new business, like for example, startup. To have a really good understanding and have enough data from your podcast to actually know if it works, you need ideally a year of weekly episodes. A lot of podcasters stop too early. They start a podcast, they do a few episodes. Consistency is extremely difficult, but within that year, you can truly know if this works or doesn't work.
Dr. Shalabh Gupta, is a physician turned entrepreneur who's built multiple biotech startups focused on cancer and kidney disease treatments. Shalabh brings a unique perspective to entrepreneurship, applying lessons from his medical background to the high stakes world of life sciences startups.
In this episode, we explore the real motivations behind starting a company and why fame and fortune should never be your primary drivers. Shalabh shares how his experiences in the ICU shaped his approach to risk and failure, and reveals the leadership principles that have helped him build successful teams.
Roberto Cipriani, the founder of Paper, elucidates the transformative journey of his educational technology company, which aims to democratize access to tutoring across North America. Launched initially as Grade Slam in early 2014, the company evolved through a rebranding in 2020, recognizing the inadequacies of its original name. Cipriani's commitment to providing affordable educational support stems from his own academic experiences and the desire to offer the same support he received to those in need.
The salient point of this podcast conversation with Ashlee Turner is the profound importance of listening to customers and addressing their needs, which has been pivotal to her entrepreneurial journey and the creation of her innovative product, Pocket Panty. Throughout our dialogue, Ashlee elucidates her experiences as an entrepreneur, beginning from her early ventures to her current focus on providing women with practical solutions to their intimate needs. The conversation delves into the various challenges she faced, including the lessons learned from her initial failure in the candy business
In our engaging discourse, we delve into the profound insights of Alessandro Grampa, a distinguished serial entrepreneur who embodies the essence of resilience and adaptability in the ever-evolving landscape of startups. Alessandro elucidates the pivotal notion that entrepreneurship transcends mere career choices, evolving into a comprehensive lifestyle commitment marked by profound personal dedication and understanding. He candidly shares his transformative journey through the challenges of ADHD and depression, revealing how these adversities catalyzed his exploration of biohacking and meditation
Zara Haji Hashemi's journey from Iran to the United States is emblematic of resilience and innovation, and serves as the focal point of our discourse. In this episode, we delve into her profound commitment to transforming women's healthcare through artificial intelligence, particularly as the founder of Cybele Health. Zara elucidates on her academic endeavors, including her PhD in AI and healthcare, and her impactful tenure at Apple
Krenar Komoni, the founder and CEO of Tive, joins us to elucidate the transformative impact of real-time tracking technology on supply chain visibility. His journey from an immigrant in Kosovo to a successful entrepreneur in Massachusetts exemplifies the resilience and determination inherent in the immigrant founder experience. Throughout our discussion, Krenar recounts the pivotal moments that shaped his entrepreneurial path including the near-bankruptcy of Tive with only $20,000 left in the bank and the profound influence of his mother's courage as a war reporter
In this episode of "Designing Successful Startups," host Jothy Rosenberg interviews Sarah Porter, founder of MedDefend. Sarah shares her personal journey from being misdiagnosed for five years (visiting over 35 specialists) to creating an AI-powered platform that helps patients with chronic conditions get properly diagnosed. She explains her battle with POTS (Postural Orthostatic Tachycardia Syndrome), which affects the autonomic nervous system, and how this experience inspired her to create technology that empowers patients and educates healthcare providers. The episode highlights how MedDefend uses AI to analyze patient data, create diagnosis roadmaps, and provide nurse coaching to help patients navigate the healthcare system more effectively. Sarah's startup journey includes raising funds through Techstars and angel investors while working to reduce the average seven-year diagnosis time for chronic conditions.
In this episode of "Designing Successful Startups," host Jothy Rosenberg interviews Håkan Andersson, a Swedish entrepreneur now based in New York. Håkan shares his journey with Establish, a logistics consulting firm he originally built, sold, and then bought back when it was failing. Rather than using traditional consulting approaches, Håkan implemented a radical transparency model - making their methodologies completely visible online, simplifying their service offerings from 70+ to just four core services, and letting customers find them rather than chasing leads. This approach helped him rebuild the company after being "airdropped" into New York with no network. Håkan also discusses surviving COVID when their entire pipeline disappeared in 10 days, the importance of maintaining a cash buffer, and his family history including his grandfather's legendary party that burned down their 500-year-old family farm. The episode highlights the value of transparency, focused offerings, and financial resilience in business.
In this episode of "Designing Successful Startups," host Jothy Rosenberg interviews Jesse Fittipaldi, an entrepreneur from Eugene, Oregon. Jesse shares his journey with Arcimoto, an electric vehicle startup that created an innovative three-wheeled EV designed for an autonomous future. He discusses securing initial investment from banker Bill Hambrecht, raising $19.5 million through a regulation A IPO, and the challenges of disrupting the automotive industry with a fraction of the usual budget. Now leading a biotech startup focused on neurological disease treatments, Jesse remains driven by his core purpose: making the world better. The episode highlights the importance of purpose-driven innovation, community impact, and resourceful thinking in entrepreneurship.
The primary focus of our discussion with Ken revolves around the mission of Bioforge, which seeks to revolutionize the manufacturing processes of precision biological medicines, particularly cell and gene therapies. Ken articulates the vision of making these groundbreaking treatments more affordable and accessible, addressing the unsustainable costs that currently range from hundreds of thousands to millions of dollars per treatment. Throughout our conversation, we explore the intricate dynamics of innovation and the translational journey from scientific discovery to practical applications that can significantly enhance people's lives.
Jeffrey Van Dyk elucidates the pivotal concept of "innovating the invisible," which serves as the cornerstone of his professional endeavors. Through his extensive experience, he aids entrepreneurs in articulating their visionary ideas and formulating market strategies that resonate with unmet needs in their industries. This episode explores the categorization of entrepreneurs into four distinct types—replicators, synthesizers, innovators, and visionaries—each contributing uniquely to the entrepreneurial landscape.
The conversation with Sam Morris elucidates the profound journey of adaptation and resilience that arises in the face of life-altering challenges. Following a catastrophic spinal cord injury that rendered him paraplegic, Sam shares his experience of navigating the complex interplay between acceptance and the instinct to fight against perceived limitations. He emphasizes that true strength lies not in battling one's circumstances, but in embracing them.
Gwenael “Gwen” Hannema is a mechanical engineer by training and a MedTech entrepreneur at heart. As the founder of OrthoSens, he is on a mission to revolutionize post-surgical recovery by "making implants talk." His company develops smart sensors and the SensApp platform to provide continuous, real-time insights into orthopedic recovery, empowering surgeons with dynamic data and engaging patients in their own healing journey.
Roger Espasa, the esteemed founder and CEO of Semi Dynamics, engaged in a profound discourse on the intricacies of innovation within the realm of high-performance computing and machine learning. Central to our conversation was the notion that the journey of entrepreneurship is fraught with challenges, yet it is the persistent pursuit of completion and excellence that defines success. Espasa articulated his personal motivations for founding Semi Dynamics, stemming from experiences in larger corporations where pivotal projects were often abandoned, leaving him with a profound sense of frustration
David and Jothy reminisce about their long-standing friendship and their shared experiences in the tech industry, with a particular focus on their time at Borland. The conversation delves into the importance of strong teams and customer relationships in developing quality software. They reflect on their individual career paths, highlighting key moments that shaped their understanding of technology and management. Jothy shares his journey through various startups, emphasizing the value of grit and resilience in the face of challenges.
Analisa Gooden, founder and CEO of Catch and Release, discusses her innovative approach to licensing content from the internet, addressing the complexities of intellectual property in the digital age. Her company aims to create a seamless licensing layer that connects content creators with brands, ensuring that creators are fairly compensated while brands can utilize authentic content for their marketing campaigns. Gooden shares her personal journey, from her early experiences with entrepreneurship to navigating the challenges of transitioning from a service-based model to a product-focused company.
Vivjan Myrto, founder and managing partner at Hyperplane, shares his extraordinary journey from growing up in Albania under a harsh communist regime to navigating significant health challenges, including a battle with cancer, which ultimately shaped his resilient entrepreneurial spirit. He reflects on the lessons learned from surviving societal upheavals and how they instilled a deep determination to persevere and innovate. Vivjan emphasizes the importance of grit and adaptability in the startup world, highlighting that success often comes from being reactive to the present rather than overly focused on long-term predictions.
More About the Podcast
I lost my right leg and left lung to bone cancer by the age of 19. I had no choice but to develop grit just to survive. Then starting at age 32 I founded and ran a total of 9 tech startups and I sure needed the grit I had already developed to do that. Truth is, grit is needed whenever we take on something really difficult. In this podcast we will visit with people from those two very difficult pursuits as well as others. This podcast is full of advice on how to develop grit for whatever tough things you need to tackle including on how to tackle the great challenge of creating a new tech business out of thin air. My guests and I will convey our valuable startup experience via sometimes amusing stories, happily admitting our mistakes, but always helping the audience know the right way to build a successful startup that will be headed in the right direction the right way, maximizing its chances to become a profitable business. And you will be inspired when the guest is someone like Hugh Herr who lost both legs below the knees to frostbite while ice climbing. He has since gone on to be a world class climber but also the leading developer of bionic prosthetics in the world. There are hundreds of people as inspiring as Hugh. You will get to meet lots of them.
Jothy Rosenberg interviews Fabricio Costa, a Brazilian scientist turned entrepreneur with experience at Harvard, Apple, Amazon, and Accenture. Fabricio shares his journey from PhD researcher to startup founder, detailing costly mistakes like raising capital too early and diluting equity. He discusses his work developing technology to diagnose rare genetic diseases faster, his time leading Apple's developer programs in Brazil, and his current AI consulting work. The conversation covers AI hype versus reality, job displacement concerns, and the importance of AI literacy. Fabricio's grit story involves persisting through 30+ journal rejections before publishing groundbreaking research on non-coding RNA.Retry