Maddy Niebauer on Peace Corps Lessons and Building The Chiefs

Maddy Niebauer on Peace Corps Lessons and Building The Chiefs

We sit down with Maddy Niebauer to trace the experiences that shaped her early mindset. She reflects on growing up in the Bay Area, moving often, and changing schools year after year. As a result, she learned to adapt fast, make friends quickly, and keep going through disruption. She also explains how high academic expectations at home pushed her to take school seriously, even when the pressure felt heavy. Maddy Niebauer and the search for direction From there, the conversation moves into college and the uncertainty that comes with choosing a path too early. She shares why she started college undecided, why psychology pulled her in, and how research first seemed exciting. However, one long project with inconclusive data changed her view of academic work. That moment forced her to question what kind of future she wanted. It also opened the door to a wider conversation about discovery, curiosity, and the limits of rigid career planning. In that sense, fractional leadership starts with learning how to step back and reassess your role. West Africa changed the frame After college, Maddy joined the Peace Corps and spent more than two years in Ivory Coast. That chapter gave her a direct view of service, shared responsibility, and daily life in a communal culture. She describes how family structures, work, and even simple tools carried a different meaning there. Because of that, she returned with a stronger sense of perspective and a deeper interest in mission driven work. Later, that same perspective shaped how she viewed management, nonprofit impact, and fractional leadership in practice. Building The Chiefs with Maddy When she returned to the United States, she worked in education, earned an MBA at Columbia, and later moved into nonprofit consulting. Eventually, a chief of staff role at Teach For America became the turning point. She didn’t chase that title at first, yet the work fit her strengths. Then layoffs pushed her to make a decision. Instead of starting over in another job, she turned a side engagement into a business. That move became The Chiefs, a company built around part time executive support. Here, fractional leadership became more than an idea. It became the service itself. What Maddy learned about letting go We also talk through the messy parts of building a company. She explains early pricing mistakes, unclear project scope, and the cost of being too accommodating. More importantly, she shares what changed when she stopped trying to do everything herself. Her decision to hire support, build systems, and later work with a co CEO gave the business room to grow. At the same time, it gave her more freedom. That lesson sits at the center of this episode. Fractional leadership helps leaders focus on what only they can do. In the end, fractional leadership works best when trust, structure, and self awareness all grow together. Chapters 00:00 Welcome to Founders Journey 01:07 Meet Maddy Niebauer 01:31 Growing up in the Bay Area 05:12 What changing schools taught her 09:11 College pressure and choosing a path 20:21 Peace Corps work in Ivory Coast 26:21 Tutoring centers and social enterprise 28:24 Columbia MBA and nonprofit consulting 36:19 Teach For America and chief of staff work 40:30 Starting The Chiefs and letting go as a founder

Randy Johnston on Building Technology Leadership That Actually Helps People

We talk with Randy Johnston about the kind of childhood that builds real problem solvers. He grew up in Hutchinson, Kansas, and learned by asking questions. He learned from mechanics, carpenters, electricians, and architects in his own neighborhood. As a result, he built a practical mindset early. That mindset shaped his approach to technology leadership long before he entered business. A curious start with Randy Johnston Randy also explains why listening matters more than status. He says you can learn from almost anyone, if you ask and stay quiet. That lesson runs through the whole conversation. It also explains why his work in technology leadership stayed focused on people, not prestige. Randy Johnston on choosing service over scale Later, we get into the choices that shaped his career. He turned down a job with IBM because he wanted to stay rooted in Kansas. That decision looked limiting at first. However, it opened a different path. He moved from programming to teaching, then into product design, consulting, and entrepreneurship. Along the way, technology leadership kept showing up through service, teaching, and thoughtful execution. He shares how he helped build products many people still use. That includes work tied to Microsoft Office, Excel pivot tables, ThinkPad TrackPoint, and more. Yet he doesn’t frame that work as fame. Instead, he frames it as useful work. That gives this episode a grounded view of technology leadership that many founders rarely hear. Lessons from Randy Johnston that still hold up The strongest part of this conversation may be Randy’s business philosophy. He doesn’t believe bigger always means better. In fact, he chose to shrink parts of his company when growth weakened relationships. He wanted to know people by name. He wanted to stay close to the work. Because of that, technology leadership becomes less about scale and more about responsibility. We also talk about money, ethics, and judgment. Randy argues that helping people creates stronger businesses than chasing revenue alone. He warns against secrecy, ego, and empty passion. Instead, he pushes founders to improve ideas, build sound processes, and keep an outward focus. That makes his view of technology leadership especially useful for entrepreneurs building for the long term. What founders can take from this episode By the end, this episode becomes a guide to better decision making. Randy talks about family, travel, balance, trust, and choosing work that aligns with your principles. He explains why he left companies that crossed legal lines. He also explains why ideas matter less than execution and improvement. So while the stories are remarkable, the real value sits in the lessons. If you care about building useful products, staying ethical, and leading with substance, this conversation delivers. It shows how curiosity compounds over time. It shows why relationships still matter. And it shows how a long career in technology can stay deeply human. Chapters 00:00 Growing up curious in Hutchinson Kansas 08:15 Why asking questions builds better entrepreneurs 17:15 Randy Johnston and the early days of computing 30:57 Vietnam era pressure and college decisions 41:02 From programmer to teacher and textbook author 42:49 Building products behind Apple IBM and Microsoft 51:00 Why bigger business is not always better 57:05 Ethics money and how founders should think 01:04:10 Family travel and balancing entrepreneurship 01:15:43 Advice for new entrepreneurs starting today

Kobi Simmat on Wealth Creation Delegation and Business Ownership

Kobi grew up in Sydney around national parks, beaches, boats, and building sites. So, work never sat in a separate box from life. His father ran an architecture and construction business, and the family often joined site visits on weekends and holidays. That early exposure shaped how he saw business, responsibility, and momentum. He didn’t describe entrepreneurship as glamorous. Instead, he saw it as a path to a more active and intentional life. That view frames the whole conversation around wealth creation. Why Kobi Simmat values ownership He explains that many people wait to feel inspired before they move. However, he believes people can learn to become passionate through action. He also argues that earning years are limited, so building resources for your family can’t stay optional. That idea drives his view of wealth creation. He talks openly about family roles, duty, and the need to prepare the next generation. As a result, this episode becomes less about status and more about stewardship. Kobi also shares how school never fit the way he learned. He showed up, paid attention, and still struggled in a traditional classroom. Then everything changed in technical college, where discussion replaced rote repetition. From there, he became a top student and found a learning style that worked. So, one of the clearest lessons here is simple. You still need education, but you must learn how to learn. The lesson Kobi Simmat would pass on Later, he walks through the business he built in construction consulting. His company helped contractors meet government standards in safety, quality, environment, and risk. The model created recurring revenue, long client retention, and a clear service structure. Yet the deeper lesson isn’t only about systems. It’s about leaving the technician role before it traps you. That shift matters because wealth creation gets harder when the owner stays buried in delivery. He tells a great story about finding a book in an airport called How to Grow Your Business by Taking Three Months Off. That idea pushed him to document work, delegate tasks, and step away. Then he actually left for South America for three months. Even during the global financial crisis, the business kept moving because the team had ownership. So, the episode turns delegation into a practical tool for wealth creation, not a soft leadership idea. By the end, Kobi makes a strong distinction between being a technician, a coach, and a shareholder. He believes too many founders stay attached to being the best operator. However, real progress starts when they train others, let people make small mistakes, and think like owners. That transition is central to wealth creation because it creates space, leverage, and long term value. We also hear how he brought forward years of earnings by selling his company, and why that sale fit his larger plan for family wealth, learning, and responsibility. Chapters 00:00 The book that changed how he ran business 00:00:57 Meet Kobi Simmat from Australia 00:02:31 Growing up with an entrepreneur father 00:05:21 Why work shaped every family holiday 00:10:07 His 5 AM routine and drive to keep moving 00:12:14 Why founders must build family wealth early 00:24:18 How he teaches business books to his son 00:26:05 Why school failed and discussion helped him learn 00:33:02 Choosing construction and business ownership 00:46:01 How delegation helped him take three months off

Jonathan Aberman on Resilience Creativity and Building Through Change

We sat down with Jonathan Aberman to trace the roots of his entrepreneurial mindset. He shares how an unstructured childhood in Philadelphia shaped the way he thinks, creates, and adapts. That early freedom became the foundation for entrepreneurial resilience. He also reflects on growing up in a multicultural city, around artists, small business owners, and family instability. Because of that mix, he learned to read people, handle ambiguity, and keep moving. Those lessons still define his entrepreneurial resilience today. Aberman on real resilience Johnathan challenges the idea that comfort builds capable people. Instead, he argues that resilience comes from adversity, friction, and the need to solve problems without a script. So this part of the conversation turns entrepreneurial resilience into something practical for parents, educators, and founders. He talks about school, creativity, and why too much structure can limit independent thinking. Then he explains why many young people struggle with setbacks, even when they have talent. However, he also believes that resilience can be taught through expectations, accountability, and real experience. What Johnathan learned by building Later, we move into his career, from law and banking to venture capital and company building. He explains the push and pull that led him away from prestige and toward ownership. That shift reveals how entrepreneurial resilience grows when people choose autonomy over comfort. He also breaks down how he evaluates founders, why self awareness matters, and what he looks for before backing an idea. For him, great businesses rarely start polished. Instead, they evolve through small wins, honest feedback, and teams that can adapt under pressure. The episode also explores AI, originality, and the risk of becoming passive in a world built for convenience. Johnathan argues that tools can help, yet they can also flatten thinking. So the people who stand out will pair technology with judgment, toughness, and entrepreneurial resilience. This conversation offers a sharp look at creativity, purpose, investing, and the mindset behind building anything meaningful. We think it will resonate with founders, operators, parents, and anyone facing a hard pivot. It’s a thoughtful reminder that growth starts when comfort ends. Chapters 00:00 Podcast intro and episode setup 01:08 Jonathan Aberman on growing up in Philadelphia 07:28 Family business roots and early entrepreneurial exposure 09:12 Creativity school and an unstructured childhood 12:39 Why kids need grit and less overprotection 18:05 AI originality and the future of human value 22:23 First jobs autonomy and learning to work early 27:27 Leaving law to build an entrepreneurial life 44:18 How dealmakers manage ambiguity and momentum 50:52 What investors really look for in founders

Allen Kopelman on transparent pricing sales and building through hard work

We sat down with Allen Kopelman to trace a path shaped by family business, restaurant kitchens, and long-term entrepreneurship. Early on, he grew up around clothing stores, factory work, and old-school retail. As a result, he learned cash handling, customer service, and negotiation before adulthood. That background still shapes how he sees transparent pricing today. He explains how his parents influenced his work ethic and judgment. His mother showed him how to negotiate. Meanwhile, his father taught him to treat every job like it belongs to your family. That lesson stayed with him through every chapter. It also became the basis for his view of transparent pricing. From kitchens to business ownership with Allen Before payments, Allen built a serious career in hospitality. He worked in restaurants, entered culinary training, and moved through demanding hotel kitchens. Then he became an executive chef before age thirty. Along the way, he learned menu costing, purchasing, operations, and how to stay calm under pressure. Later, he opened his own restaurant in Boca Raton. However, the next chapter arrived when promises from employers stopped matching reality. That pushed him to explore merchant services. Because he already knew the pain points of processing payments, he saw the business clearly. He didn’t want confusing terms or surprise changes. Instead, he wanted transparent pricing that owners could actually understand. Allen Kopelman on sales trust and long term resilience Allen also makes a strong case for sales as a core business skill. He says entrepreneurs can’t avoid it. You need to speak clearly, build trust, and ask for business directly. He credits Dale Carnegie with helping him find his voice. That growth helped him lead, present, and sell with more confidence. He also shares what 25 years in payments taught him. Partnerships matter. Reputation matters. And fairness matters most when problems show up. He wants clients to know the fees, the options, and the risks before they sign. That commitment to transparent pricing reflects how he wants to be treated himself. Toward the end, he gives practical advice for younger entrepreneurs. Keep overhead low. Learn sales early. Build real skills that solve real problems. Also, stay organized and show up ready to work. He believes hard work still gets noticed, especially when it comes with consistency. In the end, this conversation comes back to transparent pricing, useful skills, and a mindset built for the long run. More from Allen Kopelman https://allenkopelman.com/ Chapters 00:00 Welcome to Founders Journey 01:07 Allen Kopelman on growing up in family business 03:56 How credit card processing worked in retail 07:15 Moving to Atlanta and learning new trades 12:45 Bad student strong business instincts 18:11 Inflation wages and today’s cost pressures 25:28 Entering hospitality and chef training 33:19 Why Allen left restaurants for payments 39:00 Sales trust and transparent pricing 51:56 Advice for young entrepreneurs today