
Unlearn
The way to think differently is to act differently and get comfortable with being uncomfortable. For business leaders, entrepreneurs, managers and anyone who wants to improve how they work and live: Welcome to the Unlearn Podcast. Host Barry O’Reilly, author of Unlearn and Lean Enterprise seeks to synthesize the superpowers of extraordinary individuals into actionable strategies you can use—to Think BIG, start small and learn fast, and find your edge with excellence.
Latest episodes

Nov 9, 2022 • 32min
Following Your Intellectual Curiosity with Sharena Rice
Sharena Rice is a neuroscientist, cybernetician, and storyteller. As an advisor and consultant to startups, she works at the intersection of artificial intelligence and natural intelligence, and health and wellness. Her life’s goal is to take as much suffering in as she can in this lifetime and invert it. Focused on her health and wellness domain, Sharena helps Nobody Studios through her background knowledge of biomedicine and startup skills. In this episode of Unlearn, Sharena shares her experience as a systems neuroscientist and how it has helped her in life. She and Barry O’Reilly discuss the importance and benefits of trying hard things, and debunk some misconceptions about cybernetics.
Getting Good at Failing
Doing hard things forces you to get out of your comfort zone. As a self-described former high school band geek, Sharena shares that music, especially jazz, teaches you a lot about experimentation and improvisation. In trying things that are initially hard, you put yourself in the position to be uncomfortable. By consistently doing this, you slowly get acclimated to practice and failing, which progressively grows your capabilities. It also has the added benefit of reducing your levels of self-consciousness. “Success and failure are just feedback mechanisms,” Sharena claims. They tell you if you’re going in the right direction or if you need course-correcting. “You have to keep attempting as you go through that process, rather than getting caught up in how successful you are, or how you failed.”
The Career Crossroads
Barry asks Sharena about her diverse career and how she got started. Sharena majored in biochemistry and double minored in philosophy and psychology in undergrad, but she didn’t feel as if she belonged in just one of those three boxes. There were elements of all fields that spoke to her, and she found herself conflicted on what path she should take. After linking them all together, she realized the common thread they all shared had something to do with the mind. Neuroscience was the perfect mix. She discovered, with the help of her advisor in grad school, that she was a systems neuroscientist. And from there, she found another passion in cybernetics.
Tech for Situational Understanding
Sharena debunks some misconceptions about what makes for good technology. Most people think of artificial intelligence and machine learning when they hear of cybernetic technologies - humanizing technology, to be specific. Rather than making technology human, it may be best to make technology that has great situational understanding so it can be great at solving the problems it encounters.
Finding the Next Right Thing
Barry asks Sharena to disclose some tips for figuring out the next step. “[My] biggest thing is [my] orientation towards figuring out how to make the biggest positive impact in this lifetime,” she responds. “How do I take as much suffering as possible and invert it? That’s a different equation than if someone were to ask how they can help people in a certain domain.” Rather, it’s a big and overarching goal.
Looking Ahead
Sharena is currently working as a research scientist for a public benefit corporation in medical technology.
Read full show notes at BarryO'Reilly.com
Resources
Sharena Rice on the Web | LinkedIn | Twitter

Oct 26, 2022 • 38min
Balancing Introversion with Leadership with Min Bhogaita
Min Bhogaita is Managing Director of the IdeaLab at Nobody Studios. Since leaving Deloitte, where he worked for 25 years, Min has helped over 14 startups and scaleups grow, pivot, and connect. He also serves as an advisory board member and director for multiple organizations. In this episode of Unlearn, Min shares his experience in the corporate world, and he and Barry O’Reilly emphasize the importance of staying true to yourself. They also discuss how technology is changing the way we work and how startups can benefit from this change.
Balancing Introversion with Leadership
Min admits to struggling with speaking up. During his school days, his teachers would talk about how quiet he was in class and his aversion to speaking unless spoken to. This was something he had to unlearn when breaking into the corporate world. “I was fortunate in the leaders I worked for - they knew my style, so they would coach me,” he shares. They would intentionally create opportunities for Min to share his ideas and opinions, which gradually taught him to come out of his shell and learn that behavior. “If you can recognize that there are behaviors you need to change, [you should change them].” In a serendipitous turn of fate, it was when he was learning to speak up that Min got to start his own team.
Building Confidence
Barry asks Min about his leadership experience in various fields. One of the traits Min developed was confidence in himself every time he changed a role. Min admits that he was actually a novice when he transitioned from ethical hacking to forensics. A recruiter’s recommendation that he’d be good in the field inspired him to go into it. “Just because he believed in me, I [went for it],” he tells Barry. “Thirteen years later, I was still in that role and doing the world’s biggest fraud investigations.”
Protecting Your Team
If you don’t have the right environment, people are going to burn out. This was made evident during the pandemic, but it was true even before then. Min talks about protecting his team to prevent that burnout. “Sometimes [we’d get] a deadline, and I’d push back.” If a deadline was Friday, but the document review was Tuesday, he’d request that submission be moved to late Monday to prevent his team having to work through the weekend. If you’re always pounding your team, he adds, they’re not going to do their best work.
Reinventing Min
Min talks about his decision to move on from consulting. After having worked in the field for 25 years, he thought it was now or never; he was either going to do it until he retired, or he would reinvent himself again. He was doing more work with founders and startups in the analytics lab, and grew more and more attracted to the practicality of their work. When he left consulting, his network started buzzing. People were reaching out to him, asking him to help them open the door - which, coincidentally, was his open door to new work. “I’ve made more of a living out of who I know as opposed to what I know,” he jokes.
Looking Ahead
Min’s dream is to have IdeaLabs for Nobody Studios around the world, where people can come in, share their ideas, and get started.
Read full show notes at BarryO'Reilly.com
Resources
Min Bhogaita on LinkedIn | Twitter

Oct 12, 2022 • 29min
The Importance of Mentorship with Bobby Soper
Bobby Soper is former president & CEO of Mohegan Sun, and current president & CEO of Sun Gaming & Hospitality. Initially beginning his career in law, Bobby moved into the role of CEO where he had the opportunity to lead an incredible operation. Through mentorship guidance, he learned how to lead great teams. Today, Bobby is the Investor and Chairman of the Hospitality Board at Nobody Studios, helping to build companies that will innovate and disrupt the future. In this episode of Unlearn, Bobby and Barry O’Reilly explore mentorship guidance, servant leadership, and the gaming industry.
The Role of a Mentee
Bobby attributes much of his growth and success to having a great mentor. Bill Gallardo was an exemplary role model who taught him, through demonstration, the importance of respect, humility, relationships, and hard work. Bobby shares how he cultivated that relationship and talks about the role of a mentee. “Sometimes people feel like they can reach out to anyone and hopefully ask them to be a mentor, but what you're talking about is putting yourself out there, doing hard work and demonstrating excellence,” Barry comments. Through that effort, more opportunities will come.
How Mentorship Actually Works
Mentorship is more organic than approaching someone you admire and asking them to mentor you, Bobby shares. A better approach would be to ask if you can shadow them for a day. You’ll learn more from working with them and observing how they do things than sitting with them for coffee hoping to download all their esteemed knowledge. “The measurement of my success is based on how well [the people I work with or who report to me] succeed,” he adds. “I’m very fortunate because a lot of the folks I hired… have grown and become very successful as their own CEOs. To me, that is the best measurement of my success, not how much money I make or my job title.”
Being a Good Leader
As general counsel for Mohegan Sun, Bobby’s responsibilities involved managing people. What that role taught him was that everything comes down to relationships. The most valuable education comes from being in the trenches with the ground floor workers. It teaches you how to understand people, respect them, and show them that you aren’t above them.
Technology as a Leveraging Agent
Bobby discusses what led to his advocacy for using technology to leverage customer experience. The gaming industry is young, starting in the 70s and becoming more prolific in the last 3 decades. The demand for casino gaming has existed for hundreds of years, but there wasn’t always a supply. The old adage of “if you build it, they will come” applied to the gaming industry significantly, due to the supply-demand imbalance. The problem with that, Bobby tells Barry, is that it wasn’t a competitive environment. Without competition, there’s no need for innovation. Now, the industry has matured and innovation is starting to pick up. However, some gaps remain.
Looking Ahead
Bobby believes digital is the future. When you look beyond Generation X, the customers are mostly online, and the gaming industry has to adapt. In addition, the digital systems in the hospitality industry need innovation and improvement.
Read full show notes at BarryO'Reilly.com
Resources
Bobby Soper on LinkedIn

Sep 28, 2022 • 37min
Intelligent No Code with Jason and Gareth Edge
Jason and Gareth Edge are co-founders of ThoughtForma, the intelligent no-code platform with a mission to help people unlock and realize their purposeful ideas. As CTO and CEO respectively, they aim to break the barriers to entry that technology itself often represents, and obliterate the obstacles to creativity and enterprise in the digital space. Both brothers are VPs of Technology at Nobody Studios. In this episode of Unlearn, Jason and Gareth share their story with Barry O’Reilly, discussing how they built their company and obstacles they faced in the technology space.
How It Started
Gareth shares the inspiration behind ThoughtForma. Building software is a hard thing to do and people - both individuals and organizations - often struggle during the process. Even with a team of skilled technologists with great track records, it’s still difficult to deliver robust solutions. Coupled with a shortage of technical skills, this leads to many projects never seeing the light of day. “That’s [what] puts a fire in my belly,” Gareth says, “this notion of ideas staying locked in people’s heads is completely unacceptable to me.”
A Pleasant Coincidence
Gareth pitched the idea to his brother Jason, who happened to be working on something related. “I was able to dovetail into his vision and we came up with the ideal, no-code platform, which is our answer to the Al Gore problem,” Jason explains. He approached building the platform via an unconventional route, as he had been working for a consultancy specializing in the implementation of Master Data Management Systems. He was hitting some walls in implementing these systems. Jason started thinking about how he could capture the data he wanted without having to rebuild and redesign, and how he could put such a tool in the hands of consultants so they wouldn’t have to rely on people to build things for them. “It turns out that the ideas I came up with were so flexible that you can actually apply them to describe and manage anything, even all the ingredients of a web or mobile application. That realization became the underpinnings of where we are today,” he shares.
Startup Land
It doesn’t matter how good you think your product is - you won’t escape Startup Land, Gareth advises. “I feel fortunate that I was so naive from the start,” he tells Barry. “I fell into the trap of the field of dreams. ‘If we build it, the users are going to come. Why wouldn’t they?’ That was the first unlearning for me.” They faced many hurdles in building the platform and the company. Scarcity of capital was one issue, as was the realization that they were lacking many skills. “How important marketing is, how important financial planning, how to build companies, how to build startups - it [was] all a massive learning curve.”
No-code, Serverless Technology
Jason describes how they got around technical debt. In the software space, technical debt refers to an issue in development where you gradually create a problem you’ll later have to solve. Jason got around that by using templates to write the system, rather than manually rewriting everything. This way, if he wanted to make significant changes in architectural approach, he could just change the templates and regenerate the system.
Looking Ahead
Jason and Gareth are launching a new pattern matching and recognition feature in the near future. “[This] is a key point in our growth story because that now… allows [our users] to self-service so that if they hit upon a feature that ThoughtForma doesn't currently support codelessly, they can build it themselves, and then share that back into the community.”
Read full show notes at BarryO'Reilly.com
Resources
Gareth Edge on LinkedIn
Jason Edge on LinkedIn | Twitter
ThoughtForma

Sep 14, 2022 • 27min
Standing Ovationz with Ray Leonard Jr
Ray Leonard Jr is co-founder of Nobody Studios and CEO of Ovationz, the premier talent marketplace allowing SMEs, artists, speakers and athletes to monetize their time and skills effortlessly. The son of legendary boxer ‘Sugar’ Ray Leonard, and a two-sport divisional collegiate athlete, Ray founded and sold his own sports agency, going on to become one of the great coaches, mentors and trainers for others looking to try and build businesses. His high energy and penchant for leadership drew him to the world of motivational speaking, where he is now one of the most in-demand speakers throughout the globe. In this episode of Unlearn, Ray and Barry O’Reilly explore the lessons he learned throughout his personal and professional journey.
Growing Up and Out
Appreciating the diversity of the world was something Ray was privileged to experience growing up. Traveling around and meeting people from different cultures, backgrounds, and socioeconomic levels transformed his life in many ways, teaching him how to be a good-hearted person, friend, and business person. One of the little moments that helped shape him as a person happened early on in his life. He remembers his grandfather’s advice to this day: always remain humble, because success can be temporary; when better, you do better; and don’t live life with your foot on the accelerator - sometimes you have to slow down and pay attention to the small things that matter.
Making His Way
Naivete paved the way to clearing his own path about what he wanted to achieve, Ray confesses. “I never believed I should be in anyone's shadow.” Even with all his successes, during high school and after in his professional life, it never felt like it was enough. He knew he had so much more to give after selling and exiting his sports agency, so he went back to the drawing board. His curiosity about money led him to the financial sector. Throughout this journey he experienced soaring highs and humbling lows, and though the lessons took a little time to stick, he came out of it wiser and more experienced, ready for life’s next challenge.
Ray’s Next Big Move
Ray’s first foray into motivational speaking came at the request of his business partner at the time. A military veteran, she had asked him to speak to the Navy base, as he had been doing some coaching for his kids and her kids. At first, he was reluctant - he wasn’t a public speaker, so why would he? Sure, he had some resonance with the kids when he spoke, but those were kids. Despite his concerns, he went down to the base and spoke. Then he was invited to speak again. After his second time, they offered to pay him. “I said ‘oh, that’s a thing,’” Ray tells Barry. This snowballed into ten years of traveling across the world speaking to militaries and corporations about his experiences.
Sometimes, You Have to Hit the Brakes
“A lot of times I would run so fast because I thought I had to be somewhere at a certain time, on my time,” Ray tells Barry. Life has a way of telling you that sometimes it moves on its own time. No matter how fast you think you have to move, you’re going to miss some things if you don’t slow down to appreciate them. “The greatest thing about being present in the moment to tell your story is knowing there’s more to write. You don’t take a book and skip the pages - you have to read every page to get the full context.” That’s where Ray is right now, he shares.
Looking Ahead
“We’re on the precipice of building something that not only connects people but builds a more prosperous world. It makes you want to get up every single morning to create and not worry about everything that distracts you,” Ray shares.
Read full show notes at BarryO'Reilly.com
Resources
Ray Leonard Jr on the Web | LinkedIn | Twitter
Nobody Studios

Aug 31, 2022 • 41min
Red Team Thinking and Finding Opportunities in Chaos with Bryce Hoffman
Bryce Hoffman is a bestselling author, speaker, and unconsultant who believes that individuals have the power to transform companies and cultures through great leadership and applied critical thinking. He is one of the world’s foremost experts in decision-support red teaming, a revolutionary methodology inspired by the US military and intelligence agencies to help leaders make better decisions in today's complex and rapidly changing world. In this episode of Unlearn, Bryce and Barry O’Reilly explore red team thinking, contrarian techniques and what you can learn from failure.
Getting Started
Bryce describes his experience writing his first book, American Icon. One day, after sending the meatier chapters to his editor, they called him and encouraged him to think about what consultant practice he would launch along with the book release. “I said, ‘What? I’m trying to get this book finished, what are you talking about? I’m not a consultant,’” Bryce shares. His editor believed people would be flocking to Bryce for help in implementing the ideas from his book, but he was of the opposite opinion. He just wanted to tell a story. True to his editor’s predictions, however, calls came in from left to right when the book launched.
Red Team Thinking
Bryce defines red team thinking. “[It’s] a cognitive capability that helps individuals and organizations engage in critical thinking, enable distributed decision making, and most importantly, encourage diversity of thought.” These things all come together to help people make decisions faster in the complex world we live in today. He continues, “I discovered this concept called red team decision-support that had been developed by the military and intelligence community after 9/11… that became the top of my second book.” He took the tools and techniques for the high-stakes world of military and intelligence, and imported those ideas to help business leaders apply the same approach.
Contrarian Techniques
Red Team Thinking has a group of tools called contrarian techniques, designed to challenge the plan you’ve developed and force you to come up with different options. It’s been scientifically proven that humans tend to work on a problem until they find the first viable solution and then execute that. The problem with that, Bryce explains, is that the best solution might not actually be the first one that comes to you, and because you’ve stopped there, you’ve missed the opportunity that the other one presents. “Some people say ‘I don’t have time for that.’ It’s not a matter of time, it’s a matter of perspective,” he advises.
Learning from Failure
In the corporate world, people only do things they’re confident in, Barry claims. They don’t take risks, and are afraid to be wrong because they are wary of the treatment they will receive. He finds that in innovative companies, though they may not know all the answers, they have systems in place to figure them out. They try things - some things work, and some don’t, and they use both pieces of information to take another chance and try something differently. “If you don’t have the ability to fail, you’re never going to take the risks that are required to have real innovation,” Bryce adds. Good companies are good at letting their R&D teams do this, but very few companies let their leaders do this.
Looking Ahead
Red Team Thinking is working with federal fire agencies in the United States National Park Service US Forest Service, teaching them how to use their tools and techniques to make life and death decisions on the fire line about where to deploy resources and how to work together effectively with different agencies.
Read full show notes at BarryO'Reilly.com
Resources
Bryce Hoffman on the Web | LinkedIn | Twitter
Red Team Thinking

Aug 17, 2022 • 45min
Managing Portfolios with ProductOps with Becky Flint
Becky Flint is founder and CEO of Dragonboat, the responsive portfolio platform for product teams to build products customers love and deliver business results. In her career Becky has built and scaled portfolio management at Shutterfly, Feedzai and BigCommerce. She is an expert in managing ProductOps portfolios with an outcome-focused approach. In this episode of Unlearn, she and Barry O’Reilly discuss how Dragonboat is changing the game in portfolio management, and why you should make the shift to become outcome-focused.
Finding Her Way
Becky’s entrepreneurial journey wasn’t linear. She moved to the US with a medical background to study business, then went on to do tech, until she finally found her calling in product. She founded Dragonboat by piecing together the best bits of her experiences in these industries. One of the things that emboldened her to step out her comfort zone and go into completely different domains was her confidence in her ability to learn new things. Becky believed she could build on top of the skills she already had and learn what she didn’t know. It was better than starting from zero, with no skills, knowledge or experience to speak of, she shares.
Building Dragonboat
The development of the portfolio management at PayPal was originally a connect-the-dots for certain systems, according to Becky. Data revealed business outcomes, product strategy and execution, and resourcing weren’t properly communicating, so Becky created a middle engine to put all the messy stuff together. Barry remarks, “Even a few hours ago, I was in a session with some teams… and you could see that people were struggling because sometimes their corporate strategy just feels so far removed from their day-to-day work.” Becky’s “phenomenal” portfolio management makes a typically difficult process significantly easier.
Outcomes Over Outputs
One of the biggest debates in the product management industry currently is the notion of becoming more outcome-focused, Barry comments. However, not only is it difficult, but it’s also a huge change in the way people manage their work. Most people are primarily focused on output-based measures of success, such as being on time and being on budget. Becky describes some of the growing pains she experienced in helping people shift their mindsets. “Output focus really came from the industry era… the executive would make all the calls, and the team would just do what they were told, but then we realized the executive doesn’t know everything, they don’t have the latest information, so they have to rely on the team to stay competitive,” she explains.
Making the Decision to Make a Decision
Every time you make a decision, you must consider the upside, the limiting factor of time, and the resources you have available. “Not making a decision means you already failed,” Becky advises. “You definitely don't have resources for all of them. If you want to do all of them and you don’t have the resources, everything will take forever and you won’t get any outcomes.”
Looking Ahead
“What I'm most excited to see really is the trend moving from the output-focused command and control to the outcome-focused empowerment,” Becky notes. “I really believe you need alignment to be able to empower your team. Alignment and autonomy need to come together, so not too much control or the chaos of no control.”
Read full show notes at BarryO'Reilly.com
Resources
Becky Flint on the Web | LinkedIn | Twitter

5 snips
Aug 3, 2022 • 43min
Marketing's Job To Be Done with Katelyn Bourgoin
Katelyn Bourgoin is a marketer by trade and founder by choice. She is CEO and Lead Trainer of Customer Camp, where she helps teams make smarter marketing decisions with buyer psychology. A marketing powerhouse, Katelyn has been nicknamed “The Customer Whisperer,” and called an “influential entrepreneur” by Forbes; she is also one of the Top 20 Wonder Women of SaaS Marketing and Growth. In this episode of Unlearn, she and Barry O’Reilly discuss her customer discovery journey and where she found breakthroughs where others have struggled.
Effective Customer Discovery
After a brief, failed venture into making a tech company, Katelyn discovered something about customer discovery she previously misunderstood. She knew the importance of understanding and targeting your audience, but was left stumped when she did things as she was supposed to and achieved poor results. She underestimated the true value of market research, and tried selling a solution at the start, instead of starting with the customers’ needs and working backwards to the solution.
Job to be Done (JTBD)
Your ideal customer profile shouldn’t be based solely on demographics, but on the job your customers need your product or service to help them perform. Katelyn learned the Jobs-to-be-Done (JTBD) philosophy at a webinar by Forget the Funnel and it has influenced her approach to marketing ever since. Essentially, JTBD posits that people hire products and services to help them get a job done. They will continue to use that product for as long as it fulfills their needs and circumstances, and helps them move closer to where and who they want to be. “People don’t buy products and services willy-nilly,” Katelyn explains. “...We actually have a job we’re trying to get done.” Once that solution stops working, they will find a new one.
The Buyer Journey Interview
Integrating JTBD into buyer journey interviews -also called switch interviews - is the next step in elevating your market research. Katelyn’s mentor Bob Moesta was the one to make this discovery, and it happened by accident. Due to his dyslexia, Bob would draw a timeline of his clients’ stories instead of jotting down notes since this visual method was more effective for him. While drawing these images, it hit him like a brick: customer researchers were doing interviews all wrong. They had a siloed approach to solving customer problems, focusing on a specific issue under specific circumstances rather than getting the full picture of what led a customer to them in the first place.
Who Are Your True Competitors?
Katelyn talks about April Dunford’s exercise to understand who your real competitors are, and what the real job to be done is. If your product didn’t exist, what alternative solutions would people use? What are they using right now, if not your direct competitor’s products? Getting into the layers of who your real competition is and deeply understanding the job being done helps you see your solution in an innovative way, Katelyn shares. ConvertKit is one company that is successful at this: they don’t see themselves as email marketing software, but as a platform that helps creators make a living creating. Their concierge service and their recent sponsor network program demonstrate their mission, and sets them apart from other email service providers.
Looking Ahead
In following her dream scenario of building a scalable business that doesn’t require too much of her time, Katelyn is building out her newsletter, Why We Buy, into a media company. She has halted her consulting work to focus on this new venture, which she is doing with an amazing team of contractors as opposed to individual employees.
Read full show notes at BarryO'Reilly.com
Resources
Katelyn Bourgoin on the Web | LinkedIn | Twitter
Customer Camp

Jul 20, 2022 • 42min
Exits and Acquisitions with Shawn Flynn
Shawn Flynn started his career in Beijing, China, by founding, scaling, and successfully exiting a company. He is now the Principal of a premier middle market investment bank specializing in mergers and acquisitions, capital markets, financial restructuring, and valuation. In this episode of Unlearn, he and Barry O’Reilly talk about acquisitions and exiting.
Intro to investment banking
Unlike most people in the profession, Shawn did not have an undergrad economics degree, MBA, or a jam-packed resume. He was overseas for roughly 8 years after graduating from college with a mechanical engineering degree, seizing the opportunity to travel to Costa Rica, China, Europe, and back to China, where he started a few companies. One of them did well, and the others were learning experiences. After returning to the States in 2013, he got a job as an account executive for a company that unfortunately folded, but through that experience, he was able to meet and network with many angel investors and one group who eventually took him under their wing. He became the investment director for the second oldest angel group in Silicon Valley.
Debunking misconceptions
The real work in investment banking is client-facing - keeping conversations and engagement going, making people feel comfortable, and asking the necessary questions so there’s no skeletons in the closet about the company. “The people skill is so huge in this line of work and I had no idea going into it,” Shawn confesses. “I thought if you were good at Excel, you’re a good investment banker, but in reality anyone can do that. The real skill is finding the deals, being able to build that rapport and keep everyone engaged through the entire process.”
Open door policies
When planning an exit, you actually want employees to not have heard from you or contact you with urgent news in months. That’s a sign that things can and are operating smoothly without you - exactly what you need when exiting. Everyone knows their KPIs, the systems they’re running and how to get there, and what they’re doing every quarter. You want the people at the top to be able to go for vacation any time they want and not have the company destroy itself.
Time is of the essence
Time kills all deals, Barry says. At Nobody Studios, they value getting things done in a timely fashion. The number one deal killer is time. Stall too long, and you are very likely to lose the deal altogether. Anything can happen, Shawn comments, so when you’re in the marketing phase, the prime time for closing a deal is while all parties, (the buyer and the seller) are still excited.
An emotional process
Having an outside advisor during the selling process is invaluable because they prepare you for everything - and preparation is something you will need, as exiting tends to be quite emotional. Building a company can consume much of your life, and letting go can get complicated, even when selling has been the plan all along. When potential acquirers come asking questions and trying to understand some of the decisions you’ve made, it’s easy to feel like they’re attacking you. Then, when it’s time to go out to market and you get no response after a few days, it’s disheartening.
Looking forward
Shawn is looking forward to resuming in-person events, like the half-day summit he held recently. He’s also excited about collaborating with foreign companies interested in setting up operations in the US. “People have had all these dreams built up for the last 2 years, and now they’re sharing them with the world and saying ‘I gotta catch up on 2 years of stuff, let’s move fast,’” he adds.
Please visit BarryO'Reilly.com for full show notes.
Resources
Shawn Flynn at Twitter | LinkedIn
The Silicon Valley Podcast

Jul 6, 2022 • 41min
Building Developer Platforms & Working with Mentors with Kaspar von Grünberg
Kaspar von Grünberg has extensive experience running software companies. His current role is founder and CEO of Humanitec, a product that enables companies to build internal developer platforms using their Platform Orchestrator. It enables platform engineers to build golden paths that developers love and standardizes app and infra configs by design. In this episode of Unlearn, he and Barry O’Reilly discuss becoming world class.
Becoming World Class
“I'm telling everybody who works with me: you don't have to be world class today, but you have to know, ‘What is my relative position to elite status?’" Kaspar believes that everyone can fulfill their highest potential, and that a leader’s job is to facilitate this. His father’s early advice about choosing the right advisors directly influenced his approach to leadership. He tells Barry, "There is a lot you have to learn and you have to learn that really fast." As such, having the right mentors is crucial.
Finding Problem-Mentor Fit
Mentorship is a powerful way to bolster your company’s growth, Kaspar and Barry agree. Kaspar’s experience over the years has shown that there’s a correlation between professional maturity and effective problem-solving skills. He also observed that senior and junior personnel approach problem solving differently: senior staff members usually start inquiry with basic questions before delving deeper to find answers to urgent problems. This is the model he wants all his employees to adopt, and mentorship is an effective way to make this happen. That’s why he looks for humility and coachability when hiring new talent.
Why Internal Developer Platforms Are the Future
Kaspar goes on explaining why he is so passionate about platform engineering and enabling engineering organizations to build Internal Developer Platforms. Kaspar’s experience in building software teams from the ground up several times ultimately made him understand that many of the industry challenges had psychological underpinnings. Some of these included monopolizing key projects and domains, which left businesses without knowledge when personnel left, along with concerns with abstraction. His observations were guided by the following questions:
How can you reduce cognitive load so that developers can actually focus on the business logic?
How can you design systems that drive standardization by design?
Convincing Teams of the Value of Standardization
Kaspar points out that the fear of standardization and abstraction is too often the underlying fear of being “optimized away.” He points out that this is ultimately a job of culture and communication to take this fear away. “If you don't believe that doing something faster will yield 10% more, then you don't believe in personal growth and in growth of your company,” Kaspar argues. Similarly, he believes leaders should unlearn ideas about abstraction. “Intelligent opaque abstraction that doesn't go at the expense of context, is actually a good thing for your career,” he points out. This applies to software as it applies to anything else we do. Yet if you standardize and abstract you can never do so at the expense of context.
Looking forward
Kaspar thinks platform engineering is here to stay. Every team with more than 50 developers will have a platform team by 2025. Humanitec’s Platform Orchestrator will be at the core of the Internal Developer Platforms built by these teams. His ongoing passion is the platform engineering community. “Every single day I have people reaching out and contributing and sharing ideas,” he says. “I hope that is something that continues in the end.”
Read full show notes at BarryO'Reilly.com
Resources
Kaspar von Grünberg at Twitter | LinkedIn
Humanitec
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