
Designing Successful Startups
Professor-turned-entrepreneur, and founder of nine companies, Jothy Rosenberg talks with business leaders and personal achievers.
A companion to his book Tech Startup Toolkit, the “Designing Successful Startups” podcast tells the stories of Jothy's guests as they took on the challenges of building a new startup. The lessons conveyed come from both things done right and things done wrong that can help listeners learn the best way to design their own startups to be successful. Along the way this show 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.
Latest episodes

Jun 26, 2024 • 40min
B Randall Willis has Seen and Influenced the Evolution of Digital Media
SummaryIn this conversation, Jothy Rosenberg interviews B Randall Willis, discussing topics such as the importance of a name, their backgrounds in Detroit and Boston, the evolution of digital media, the characteristics of successful startups, the role of processes in startups, and the importance of storytelling and grit in entrepreneurship.TakeawaysThe importance of one's name and its impact on personal and professional identityThe influence of Detroit and Boston on his entrepreneurial journeysThe evolution of digital media and the challenges and opportunities it presentsThe characteristics of successful startups, including a good idea, strong leadership, and adequate fundingThe role of processes in startups and the need for a balance between structure and flexibilityThe power of storytelling in engaging audiences and conveying a company's value propositionThe importance of grit and perseverance in the face of challenges and setbacksSound Bites"My records got completely screwed up [because of my name]. Everything was under a different name.""The internet as a business center has gotten extremely complicated.""Is it a good idea and is the market receptive to that good idea?”LinksB Randall’s RightAngle Consulting: https://therightangleconsulting.com/Please leave us a review: https://www.podchaser.com/AdventuresOnTheCanDoThe book Think Like a Startup Founder (early access): https://www.manning.com/books/think-like-a-startup-founderJothy’s site for speaking, podcasting, and ruminating: https://jothyrosenberg.comJothy’s non-profit foundation The Who Says I Can’t Foundation: https://whosaysicant.orgJothy’s TEDx talk on why people with a disability over-achieve: https://www.youtube.com/watch?v=PNtOawXAx5AChapters00:00 Introduction and The Significance of a Name03:04 From Detroit to Boston: An Entrepreneurial Journey07:41 Characteristics of Successful Startups22:23 The Power of Storytelling in Entrepreneurship29:36 The Role of Grit in Startup Success

Jun 24, 2024 • 44min
Data Protection: The Focus of James Oliverio and his IdeaBox
SummaryJames Oliverio, founder of IdeaBox, shares his journey from working on Wall Street to starting his own company in the cybersecurity industry. He discusses the importance of separating the roles of CIO and security officer, and the need to quantify cyber risk. Oliverio explains how his company, IdeaBox, focuses on data protection and offers services such as data risk assessments and crisis communications. He also highlights the unique features of Actifile, a product that is integrated into IdeaBox's offering. Oliverio emphasizes the importance of customer service and delivering a unique experience to clients.TakeawaysSeparating the roles of CIO and security officer is crucial for effective cybersecurity.Quantifying cyber risk is essential for businesses to understand and address their vulnerabilities.IdeaBox focuses on data protection and offers services such as data risk assessments and crisis communications.Actifile, a product integrated into IdeaBox's offering, provides unique features for data protection.Delivering exceptional customer service and a unique experience is key to success in the cybersecurity industry.Sound Bites"How do you approach cyber? Quantify it. You quantify everything else in the business.""We can protect [data] preemptively with no end user involvement.”LinksJames’ IdeaBox: https://www.ideabox.com/Please leave us a review: https://www.podchaser.com/AdventuresOnTheCanDoThe book Think Like a Startup Founder (early access): https://www.manning.com/books/think-like-a-startup-founderJothy’s site for speaking, podcasting, and ruminating: https://jothyrosenberg.comJothy’s non-profit foundation The Who Says I Can’t Foundation: https://whosaysicant.orgJothy’s TEDx talk on why people with a disability over-achieve: https://www.youtube.com/watch?v=PNtOawXAx5AChapters00:00 Introduction and Background02:53 The Importance of Separating Roles in Cybersecurity06:54 Quantifying Cyber Risk13:05 Focus on Data Protection25:01 Delivering Exceptional Customer Service35:12 Future Plans and Opportunities

Jun 19, 2024 • 44min
ViziSmart is going after the $3.9B property management software market
SummaryBianca and Mirna, co-founders of ViziSmart, discuss their journey in creating an AI-powered property management solution. Bianca, originally an artist, became a property manager and experienced the stress and lack of work-life balance that came with it. She saw an opportunity to use AI to streamline communication and coordinate maintenance in the property management industry. Mirna, with a background in cutting-edge technology, joined Bianca in creating Vizy Smart. They are currently at the MVP stage and are looking to partner with customers for product-market fit. Bianca and Mirna discuss their property management software and their plans for scaling and growth. They talk about their target market, their use of offshore developers, and their plans for expansion. They also discuss the importance of grit and resilience in the startup world, as well as their hobbies and interests outside of work. They mention their focus on the Texas and Oklahoma markets and their plans to expand nationwide. They also mention their plans for an affiliate program and partnerships to spread the word about their software.TakeawaysThe property management software market is valued at $3.9 billion in North America and is growing due to factors like the housing crisis and interest rates on mortgages.ViziSmart aims to streamline communication and coordinate maintenance in the property management industry using AI.Bianca and Mirna have identified competitors in the market and believe they have a good chance of gaining market share.They have experienced early difficulties, including IP theft, but remain confident in their ability to succeed.ViziSmart is currently at the MVP stage and is seeking partnerships for product-market fit. The property management software aims to automate manual processes and provide a more efficient solution for property managers.They are using offshore developers to build their software and are looking for talent globally.They are initially focusing on the Texas and Oklahoma markets and plan to expand nationwide.They plan to use an affiliate program and partnerships to spread the word about their software.Grit and resilience are important qualities for startup founders.They enjoy hobbies such as painting and spending time with family outside of work.LinksBianca and Mirna’s ViziSmart site: https://vizismart.com/Please leave us a review: https://www.podchaser.com/AdventuresOnTheCanDoThe book Think Like a Startup Founder (early access): https://www.manning.com/books/think-like-a-startup-founderJothy’s site for speaking, podcasting, and ruminating: https://jothyrosenberg.comJothy’s non-profit foundation The Who Says I Can’t Foundation: https://whosaysicant.orgJothy’s TEDx talk on why people with a disability over-achieve: https://www.youtube.com/watch?v=PNtOawXAx5ASound Bites"I became really interested in things like chat GPT and AI when it came out.""The combination of us is just, to me, it has been miraculous.""We bring visibility, right? That's really the bottom line.""We get to test it firsthand before anybody else does""It's okay for it to be done by somewhere else, offshore"Chapters00:00 Introduction and Background01:20 Becoming Co-CEOs and Identifying the Problem05:16 Working with an Incubator06:00 Background and Motivation08:09 Naming the Company09:22 Market Size and Potential10:23 Competition and Market Share11:51 IP Theft and Overcoming Challenges15:02 Using AI to Solve Property Management Problems18:02 Stages and Future of the Company18:59 Automating Property Management Processes19:23 Using Offshore Developers for Global Talent23:37 Focusing on the Texas and Oklahoma Market26:30 Scaling and Expanding into New Markets30:59 The Importance of Grit and Resilience in Startups33:30 Hobbies and Interests Outside of Work

Jun 17, 2024 • 38min
Simplifying Logistics in the E-commerce Industry with founder Hugh Sinclair
SummaryHugh Sinclair, the founder of Commerce Blitz, discusses the challenges of logistics in the e-commerce industry and how his SaaS company provides a solution. He explains the importance of managing inventory and distribution to avoid missing sales and losing inventory. Sinclair emphasizes the need for simplicity in logistics software and how Commerce Blitz offers a user-friendly interface. He also discusses the competitive market and differentiates his company by offering customization and maintenance services. Sinclair shares his goals of empowering small businesses and potentially being acquired by a larger company in the future.TakeawaysLogistics is a critical aspect of the e-commerce industry, and managing inventory and distribution is key to avoiding missed sales and lost inventory.Simplicity is crucial in logistics software, and Commerce Blitz offers a user-friendly interface that allows users to easily manage their inventory and sales channels.Customization and maintenance services set Commerce Blitz apart from its competitors, providing a tailored solution for businesses of all sizes.The goal of Commerce Blitz is to empower small businesses and level the playing field in the e-commerce market.In the future, Commerce Blitz aims to be acquired by a larger company in the ERP, supply chain, or 3PL warehouse space.Sound Bites"Logistics is where you make all your money, but it's also where you lose all your money.""Simplicity was the hardest part. Most systems out there are very complicated, but it's really about where is this product, I have to ship it.""Word of mouth has been our main source of customers, and we're nearly at 200 customers now.”LinksHugh’s company CommerceBlitz: https://commerceblitz.com/why-commerceblitz/Please leave us a review: https://www.podchaser.com/AdventuresOnTheCanDoThe book Think Like a Startup Founder (early access): https://www.manning.com/books/think-like-a-startup-founderJothy’s site for speaking, podcasting, and ruminating: https://jothyrosenberg.comJothy’s non-profit foundation The Who Says I Can’t Foundation: https://whosaysicant.orgJothy’s TEDx talk on why people with a disability over-achieve: https://www.youtube.com/watch?v=PNtOawXAx5AChapters00:00 Introduction and Background01:08 The Big Idea Behind Commerce Blitz07:11 Simplicity and Customer Satisfaction08:28 Building a Customer Base and Product Market Fit11:42 Differentiation and Market Segmentation15:09 Product and Services Business Models16:26 Company Size and Expansion27:34 The Importance of Grit36:52 The Future of Commerce Blitz

Jun 12, 2024 • 45min
Nick Kepler on the Challenges and Importance of Semiconductor Startups
SummaryIn this conversation, Jothy Rosenberg and Nick Kepler discuss various topics related to Silicon Valley, semiconductor startups, and the importance of grit. They touch on the history and evolution of Silicon Valley, the challenges faced by semiconductor startups, and the role of incubators like Silicon Catalyst. They also explore the personal motivations behind their passion for road biking and the drive to take on new challenges. Overall, the conversation provides insights into the dynamic nature of the tech industry and the mindset required to succeed in it.TakeawaysSilicon Valley has evolved over the years, with changes in industries and technologies, but the spirit of innovation and risk-taking remains a constant.Semiconductor startups face unique challenges due to the high cost and time required to develop and bring products to market.Incubators like Silicon Catalyst play a crucial role in supporting semiconductor startups by providing resources, expertise, and access to investors.Grit is an essential quality for success in the tech industry, as it requires perseverance, adaptability, and a willingness to take on new challenges.Personal passions, such as road biking, can provide an outlet for pushing boundaries and embracing the joy of overcoming obstacles.Sound Bites"Semiconductor hardware startups in particular are different. It's expensive and takes a long time to develop the product and generate revenue."Chapters00:00 Introduction and Background02:03 The Evolution of Silicon Valley06:03 The Changing Landscape of Semiconductor Design15:37 The Challenges Faced by Semiconductor Startups30:27 The Drive for New Challenges and Personal Passions42:09 ConclusionLinksNick’s semiconductor startup incubator Silicon Catalyst, LLC: https://siliconcatalyst.com/Please leave us a review: https://www.podchaser.com/AdventuresOnTheCanDoThe book Think Like a Startup Founder (early access): https://www.manning.com/books/think-like-a-startup-founderJothy’s site for speaking, podcasting, and ruminating: https://jothyrosenberg.comJothy’s non-profit foundation The Who Says I Can’t Foundation: https://whosaysicant.orgJothy’s TEDx talk on why people with a disability over-achieve: https://www.youtube.com/watch?v=PNtOawXAx5A

Jun 10, 2024 • 37min
The Power of Networking and Building Connections for Steven Hudspeth
SummarySteven Hudspeth shares his entrepreneurial journey, starting with his upbringing in Arkansas and his military experience. He discusses the importance of resilience and not quitting, which he learned from his family and military training. Steven then talks about his transition into the restaurant industry and his rapid rise to managing multiple restaurants. Eventually, he decided to start his own franchise in the painting industry. This led him to identify a need for better communication and automation in small businesses, which inspired him to create TMO Turbo, a software company that helps businesses streamline their processes and improve customer interactions. Steven's goal is to impact as many people as possible and give them back control of their lives and businesses.TakeawaysResilience and not quitting are important qualities for success in entrepreneurship.Networking and building connections can lead to valuable opportunities.Identifying a need in the market and creating a solution can lead to a successful business venture.Automation and streamlining processes can save time and improve efficiency in small businesses.Grit is developed through challenging oneself and pushing outside of the comfort zone.Sound Bites"TMO Turbo: Adding a Turbocharger to Your Business""Expanding Beyond Tulsa: TMO Turbo's Geographical Reach""The Impact of TMO Turbo: Doubling Revenues for Businesses"LinksSteven's TMO Turbo site: https://tmoturbo.com/Please leave us a review: https://www.podchaser.com/AdventuresOnTheCanDoThe book Think Like a Startup Founder (early access): https://www.manning.com/books/think-like-a-startup-founderJothy’s site for all podcast episodes: https://jothyrosenberg.comJothy’s non-profit foundation The Who Says I Can’t Foundation: https://whosaysicant.orgJothy’s TEDx talk on why people with a disability over-achieve: https://www.youtube.com/watch?v=PNtOawXAx5AChapters00:00 Introduction and Background07:56 Transition into Entrepreneurship: Starting a Franchise14:36 Creating TMO Turbo: Streamlining Processes for Small Businesses25:12 The Impact of TMO Turbo: Doubling Revenues for Businesses29:23 Developing Grit Through Challenges and Pushing Outside the Comfort Zone

Jun 5, 2024 • 38min
Dave Molenda is the epitome of the midwestern work ethic
SummaryIn this conversation, Jothy Rosenberg interviews Dave Molenda, discussing topics such as their Midwest roots, the importance of work ethic, and their entrepreneurial journeys. They also talk about the power of mindset and the impact of saying 'I can' versus 'I can't.' Dave shares his experience of starting and selling his first business and the importance of empowering others. They discuss the value of diversity in a team and the need to have different personalities and skill sets. Dave also talks about his podcast, Positive Polarity, and the joy he finds in connecting with and learning from his guests.TakeawaysThe Midwest work ethic is highly valued and sought after in business.Changing your mindset from 'I can't' to 'I can' can have a profound impact on your success.Empowering others and building a diverse team are key to business growth and success.Podcasts are a valuable resource for personal and professional development.Finding joy and fulfillment in your work is essential for long-term success and happiness.Sound Bites"Taking the letter T off of can't. And now I can't.""If something doesn't work, let's try something different.""Changing that I can't to I can.”LinksDave's Positive Polarity podcast site: https://positivepolarity.com/episode/the-power-of-your-words/Please leave us a review: https://www.podchaser.com/AdventuresOnTheCanDoThe book Think Like a Startup Founder (early access): https://www.manning.com/books/think-like-a-startup-founderJothy’s site for speaking, podcasting, and ruminating: https://jothyrosenberg.comJothy’s non-profit foundation The Who Says I Can’t Foundation: https://whosaysicant.orgJothy’s TEDx talk on why people with a disability over-achieve: https://www.youtube.com/watch?v=PNtOawXAx5AChapters00:00 Introduction and Midwest Roots03:11 Entrepreneurial Journey and Owning a Company07:15 The Importance of Employee Continuity09:20 The Need for Cross-Pollination in Industries12:23 The Power of Personality Diversity in a Team15:18 The Value of Grit and the Midwest Work Ethic16:36 Starting the Positive Polarity Podcast25:32 The Source of Grit and Perseverance28:24 Finding Joy and Staying Active31:48 Grandchildren and Family33:39 Final Thoughts and Appreciation

Jun 3, 2024 • 55min
The Importance of Trust in a startups legal agreements with attorney Melinda Brown
SummaryIn this conversation, Jothy Rosenberg and Melinda Brown discuss their experiences working together at Draper and the challenges they faced in setting up a spin-off company. They talk about the importance of trust in legal agreements and the difficulties of navigating intellectual property ownership. They also touch on the complexities of incubating a startup within a larger organization and the need for clear communication and understanding between all parties involved. The conversation covers various challenges and complexities in contractual relationships, the importance of clean and clear provisions, the difficulty of interpreting vague terms, the significance of memorializing agreements in contracts, the challenges of collaboration and regular deliveries, the value of protecting intellectual property, the role of grit in entrepreneurship, and the importance of passion and control in starting a company.TakeawaysSetting up a spin-off company within a larger organization requires careful negotiation and clear communication to ensure the protection of intellectual property rights.Trust is essential in legal agreements, especially when dealing with sensitive issues such as intellectual property ownership.Incubating a startup within a larger organization can be challenging, but having leaders with experience in raising money and navigating the startup ecosystem can increase the chances of success.The field of use in intellectual property agreements can be ambiguous and require ongoing negotiation as the startup develops its own IP.Interpreting vague terms in contracts can be challenging and may require establishing boundaries.Memorializing agreements in contracts is important for future reference and understanding.Protecting intellectual property is essential to prevent theft and disputes.Sound Bites"Trust is so important, right? To do the right thing.""If you're not busy, that's worrisome. Basically, that means the company's probably not going to succeed."Chapters00:00 Introduction and Background07:17 Challenges of Incubating a Startup within a Larger Organization13:25 The Importance of Trust in Legal Agreements29:44 Managing Collaboration and Regular Deliveries36:10 The Value of Protecting Intellectual PropertyLinksPlease leave us a review: https://www.podchaser.com/AdventuresOnTheCanDoMelinda's company: https://coherehealth.com/The book Think Like a Startup Founder (early access): https://www.manning.com/books/think-like-a-startup-founderJothy’s site for speaking, podcasting, and ruminating: https://jothyrosenberg.comJothy’s non-profit foundation The Who Says I Can’t Foundation: https://whosaysicant.orgJothy’s TEDx talk on why people with a disability over-achieve: https://www.youtube.com/watch?v=PNtOawXAx5A

May 29, 2024 • 45min
The scrappy edtech innovator Kayvon Touran
SummaryKayvon Touran, co-founder of Zal.ai, shares his journey in the ed tech industry and the development of his company. He discusses the importance of working in an ambiguous environment and the influence it had on his career path. Kayvon explains how Zol.ai aims to enhance learning and development in the workforce by measuring skills and competencies. He also talks about the challenges of finding product-market fit and the unconventional approach they took to funding their startup.Kayvon Touran bioKayvon Touran is a seasoned operator in early-stage tech startups with over a decade of diverse industry experience. Starting his career in sales and business development, he next transitioned into product management, and eventually a GM role. Kayvon eventually found himself immersed in edtech, and spent the past five years at Noodle.com, an edtech company based in New York. At Noodle Kayvon co-created and launched a platform for universities to manage their lifelong learning initiatives online. It was during this that Kayvon, and his then coworker/now cofounder Joe Rousseau, identified a significant gap in the market concerning organizations' ability to effectively contextualize, apply, and measure their Learning and Development spend. This realization inspired him to launch his latest venture, Zal.ai – a technology and services company that combines cutting-edge learning science and generative artificial intelligence to transform learning and development for the workforce.LinksKeyvon’s current company https://zal.ai/Please leave us a review: https://www.podchaser.com/AdventuresOnTheCanDoThe book Think Like a Startup Founder (early access): https://www.manning.com/books/think-like-a-startup-founderJothy’s site for speaking, podcasting, and ruminating: https://jothyrosenberg.comJothy’s non-profit foundation The Who Says I Can’t Foundation: https://whosaysicant.orgJothy’s TEDx talk on why people with a disability over-achieve: https://www.youtube.com/watch?v=PNtOawXAx5ATakeawaysWorking in an ambiguous environment can be exciting and impactful, leading to personal and professional growth.Zol.ai aims to enhance learning and development in the workforce by measuring skills and competencies.Finding product-market fit is an ongoing process that requires continuous evaluation and adaptation.Bootstrapping can be a viable option for funding a startup, allowing for autonomy and control over the company's direction.Sound Bites"I liked working in a highly ambiguous environment""There's a huge opportunity to help better contextualize and measure learning and development"Chapters00:00 Introduction and Background09:39 Delving into edtech32:31 Bootstrapping and funding

May 22, 2024 • 54min
The Grommet Founder Jules Pieri’s Philosophy of the Power of Saying Yes
SummaryJules, the founder of The Grommet, shares her journey from growing up in Detroit to starting and selling her company. She discusses the challenges she faced, including a lack of capital and competition from Amazon. Jules also talks about the acquisition of The Grommet by Ace Hardware and the future of the company. She then shares her experience as a venture capitalist and her role at X Factor Ventures. The conversation covers topics such as dealing with rejection, the importance of saying yes, the challenges faced by women in the venture capital industry, and the traits that startup founders need to succeed.BioJules Pieri is an Investment Partner at XFactor Ventures, an Entrepreneur in Residence emeritus at Harvard Business School, and the co-founder and former CEO of The Grommet, which she sold to Ace Hardware Corporation. Jules was named one of the “Ten Most Powerful Women Entrepreneurs” by Fortune magazine.She is the author of the 2019 book “How We Make Stuff Now” that Inc. magazine called “One of the 11 Must-Read Books for Entrepreneurs.” The best-selling book is used as part of the core curriculum in many college entrepreneurship courses. Jules is a member of the Boston Design Vision Community Advisory Board, and an advisor to the American Economic Liberties Project. Jules served on the board of the University of Michigan Alumni Association, chairing the Endowment, Digital Transformation, and Nominating Committees and serving on the President’s Advisory Committee of this independent organization serving over 600,000 alums.She studied industrial and graphic design at the University of Michigan, where she graduated summa cum laude. She was the first designer to graduate from Harvard Business School, where she played on the school soccer team.Jules grew up as the daughter of an autoworker, in the city of Detroit, and has lived and worked in France and Ireland. She has three sons and lives in Boston, and is an avid hiker, weaver, and activist for economic equality.LinksPlease leave us a review: https://www.podchaser.com/AdventuresOnTheCanDoJules’ XFactor Ventures: https://www.xfactor.ventures/The Company Jules’ founded creating a new category: https://thegrommet.com/The book Think Like a Startup Founder (early access, due out late June 2024): https://www.manning.com/books/think-like-a-startup-founderJothy’s site for speaking, podcasting, and ruminating: https://jothyrosenberg.comJothy’s non-profit foundation The Who Says I Can’t Foundation: https://whosaysicant.orgTakeawaysJules grew up in Detroit and later founded The Grommet, a product launch platform.The Grommet faced challenges such as a lack of capital and competition from Amazon.The company was eventually acquired by Ace Hardware and continues to focus on finding and promoting emerging products.Jules is now a venture capitalist at X Factor Ventures, investing in diverse founding teams with billion-dollar opportunities. Finding a way to be helpful to companies even when saying no can build stronger relationships.Being able to say yes and trust the people you work with is a key trait of successful founders.Discrimination against women and people of color is still prevalent in the venture capital industry.Grit, resilience, and tenacity are important traits for startup founders.Personal experiences and upbringing can shape a person's ability to overcome challenges and succeed.TakeawaysJules grew up in Detroit and later founded The Grommet, a product launch platform.The Grommet faced challenges such as a lack of capital and competition from Amazon.The company was eventually acquired by Ace Hardware and continues to focus on finding and promoting emerging products.Jules is now a venture capitalist at X Factor Ventures, investing in diverse founding teams with billion-dollar opportunities. Finding a way to be helpful to companies even when saying no can build stronger relationships.Being able to say yes and trust the people you work with is a key trait of successful founders.Discrimination against women and people of color is still prevalent in the venture capital industry.Grit, resilience, and tenacity are important traits for startup founders.Personal experiences and upbringing can shape a person's ability to overcome challenges and succeed.Sound Bites"Yeah, so my career has been a lot around product development.""I can take the rejection. I'm very good at it, but I don't like giving it.""You've got to be able to trust the people who work with you, that they're bringing ideas, that they're going to put their all into it."Chapters00:00 From Detroit to The Grommet: Jules' Journey14:01 The Acquisition by Ace Hardware33:23 Challenges Faced by Women in Venture Capital39:41 The Traits of Successful Startup Founders