Uploaded July 2026 | Updated September 2026, 1 week ago
Watch the full episode here: inspiredinsider.com/sasha-orloff-interview
Sasha Orloff is the CEO and Co-founder of Puzzle, an AI-powered accounting platform helping startups, small businesses, and accounting firms gain real-time financial insights through a smart general ledger. Before Puzzle, he was a serial entrepreneur, serving as Co-founder and CEO of LendUp and Co-founder & Advisor to Mission Lane, with previous ventures collectively raising over $1 billion. Sasha also hosts the “Tech Finance” with Sasha Orloff podcast, where he interviews leaders shaping the future of finance and accounting.
In this episode of the Inspired Insider Podcast, Dr. Jeremy Weisz talks with Sasha Orloff, CEO and Co-founder of Puzzle, about transforming accounting with AI. They cover rebuilding systems for the AI era, using AI for accuracy over speed, why strong accounting drives growth, and strategies for adoption, customer trust, and go-to-market in a conservative industry.
Watch the full episode here: inspiredinsider.com/sasha-orloff-interview
Sasha Orloff is the CEO and Co-founder of Puzzle, an AI-powered accounting platform helping startups, small businesses, and accounting firms gain real-time financial insights through a smart general ledger. Before Puzzle, he was a serial entrepreneur, serving as Co-founder and CEO of LendUp and Co-founder & Advisor to Mission Lane, with previous ventures collectively raising over $1 billion. Sasha also hosts the “Tech Finance” with Sasha Orloff podcast, where he interviews leaders shaping the future of finance and accounting.
In this episode of the Inspired Insider Podcast, Dr. Jeremy Weisz talks with Sasha Orloff, CEO and Co-founder of Puzzle, about transforming accounting with AI. They cover rebuilding systems for the AI era, using AI for accuracy over speed, why strong accounting drives growth, and strategies for adoption, customer trust, and go-to-market in a conservative industry.
![[SaaS Series] AI, Global Talent, and the Future of Software Teams With Matt Watson](https://i.ytimg.com/vi/NWot0WTyn9k/mqdefault.jpg "[SaaS Series] AI, Global Talent, and the Future of Software Teams With Matt Watson
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Matt Watson is the Founder and CEO of Full Scale, an offshore software development company that helps U.S. companies build dedicated software engineering teams in the Philippines. A four-time tech founder and longtime CTO, he previously co-founded VinSolutions, an automotive software company that AutoTrader.com acquired in 2011, and later founded the developer-tools company Stackify. Matt brings more than 20 years of engineering and startup leadership experience to helping companies build and scale high-performing software teams. He is also the author of Product Driven and host of the Startup Hustle podcast.
Here’s a glimpse of what you’ll learn:
• [0:00] Intro
• [3:38] Matt Watson on Full Scale’s accidental beginnings and rapid growth through software talent in the Philippines
• [7:36] Key hiring and leadership lessons from building and scaling Stackify
• [16:52] How staff augmentation helps companies extend their in-house software teams
• [20:28] Best practices for integrating Philippines-based developers into distributed software teams
• [23:42] Matt’s use of AI, MCP servers, and plugins to streamline business operations
• [29:40] How AI search is transforming website traffic, marketing, and content strategy
• [34:49] Lessons and standout guests from more than 1,300 episodes of Startup Hustle
• [40:28] Why Matt believes AI is increasing the need for product thinking and human judgment
In this episode…
As AI transforms how companies build software, they are rethinking what it takes to scale development teams without sacrificing quality, speed, or accountability. With global talent and increasingly capable AI tools changing the economics of software development, how can leaders build teams that are both more efficient and more effective?
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![[Top Resource Series] Tools and Ideas Behind Smarter Growth With Douglas Feller and Tom Ruwitch](https://i.ytimg.com/vi/O1lsDrPeswY/mqdefault.jpg "[Top Resource Series] Tools and Ideas Behind Smarter Growth With Douglas Feller and Tom Ruwitch
Douglas Feller is the Founder of MyHarvest, a personal growth platform offering free courses, career resources, housing support, and tools to help people build stability and opportunity. An entrepreneur with experience in real estate investing and asphalt business ownership, he rebuilt his career after serving time in federal prison, later building and selling his asphalt company. His own experience with the challenges of reentry helped inspire MyHarvest’s mission. Today, Douglas focuses on creating resources that support personal growth, skills, second chances, and stronger paths forward for people from diverse backgrounds.
Tom Ruwitch is the Founder and CEO of Story Power Marketing, a marketing company that helps experts create compelling, client-attracting content through storytelling. A content marketing pioneer with more than 30 years of experience, he helps business leaders turn expertise into clear messaging, stronger connections, and business growth. He is also the Founder and CEO of Implementum, which combines strategy, technology, and done-for-you teams to simplify and accelerate growth. Earlier, Tom founded email marketing company MarketVolt in 2001, expanding his work in digital marketing, automation, and business growth.
In this episode… Sustainable growth rarely comes from adding more tools, tactics, or ideas just for the sake of doing more. The real advantage comes from choosing resources that sharpen your thinking, strengthen your systems, and help you act with greater intention. So what does smarter growth actually look like in practice?
Douglas Feller and Tom Ruwitch suggest that smarter growth comes from combining the right resources with focused systems, practical learning, and a willingness to keep improving. They highlight the value of mentors, specialization, proven frameworks, technology, and curiosity as tools for making better business decisions. Douglas emphasizes learning through experience, surrounding yourself with strong mentors, and knowing when to focus on a specific niche, while Tom stresses connecting strategy, technology, and team into one cohesive system. Tom also explains how customized AI and automation can turn conversations and existing content into useful marketing assets rather than generic output. Together, their insights show that sustainable growth is less about chasing every new tactic and more about building systems that help ideas translate into consistent action.
In this episode of the Inspired Insider Podcast, Dr. Jeremy Weisz speaks with Douglas Feller and Tom Ruwitch about the tools and ideas behind smarter growth. They explore valuable business resources, stronger marketing systems, and practical uses of AI and automation. Douglas and Tom also share lessons on mentorship, storytelling, curiosity, and turning knowledge into action.")
![[Beverage Series] How Pickle Juice Stops Muscle Cramps With Filip Keuppens](https://i.ytimg.com/vi/OG6gZN6trh0/mqdefault.jpg "[Beverage Series] How Pickle Juice Stops Muscle Cramps With Filip Keuppens
Filip Keuppens is the CEO of The Pickle Juice Company, a leading functional beverage brand known for its science-backed sports drink designed to help stop muscle cramps. Under his leadership, the company has expanded to more than 17,000 retailers across the US and is trusted by elite athletes and professional sports teams. Before leading The Pickle Juice Company, Filip built deep experience in sales, marketing, and retail at major companies, including Kraft Heinz, Warner Home Video, and 20th Century Fox. He is passionate about advancing sports hydration through science, innovation, and consumer education.
In this episode… Muscle cramps can strike without warning and derail athletic performance. But what if relieving a cramp had less to do with electrolytes and more to do with your nervous system? What does science reveal about how to stop muscle cramps almost instantly?
For Filip Keuppens, a consumer products executive and endurance athlete, muscle cramps are primarily a neurological issue rather than simply the result of dehydration or electrolyte loss. He explains how years of scientific research led to the development of a proprietary formula that interrupts the nerve signals responsible for cramping in 60 seconds or less. He also discusses the challenge of educating consumers about the difference between a scientifically formulated product and ordinary pickle brine. Beyond the science, Filip shares how authentic athlete advocacy, strategic retail partnerships, and a values-driven culture have fueled the companys growth while building trust with consumers. He also offers insights into launching products in major retailers, cultivating loyal brand ambassadors, and using AI to improve business operations.
In this episode of the Inspired Insider Podcast, host Dr. Jeremy Weisz sits down with Filip Keuppens, CEO of The Pickle Juice Company, to discuss building a science-backed performance beverage brand. They explore the neuroscience behind muscle cramp relief, strategies for expanding into major retail chains, and the power of ambassador marketing. Filip also shares how AI is being explored to improve business efficiency while supporting long-term growth.")
![[Top Agency Series] Scaling Revenue Through Innovative Affiliates With Rick Gardiner](https://i.ytimg.com/vi/OJ_03Ki7eow/mqdefault.jpg "[Top Agency Series] Scaling Revenue Through Innovative Affiliates With Rick Gardiner
[Top Agency Series] Scaling Revenue Through Innovative Affiliates With Rick Gardiner")
![[Venture Capital Series] How Venture Capital Really Works Beyond the Myths With Mike Collins](https://i.ytimg.com/vi/OKPTw73LZSg/mqdefault.jpg "[Venture Capital Series] How Venture Capital Really Works Beyond the Myths With Mike Collins
Mike Collins is the Founder and CEO of Alumni Ventures, a leading venture capital firm that enables individual accredited investors to access diversified venture portfolios and co-invest alongside top-tier VCs. He is a serial entrepreneur and experienced venture capitalist who has founded multiple companies, including Kid Galaxy, Big Idea Group, and RDM. He also launched Green D Ventures, Alumni Ventures’ first alumni fund, where he oversaw the portfolio as Managing Partner. Mike has spent his career helping investors and entrepreneurs build innovative, high-growth businesses, and holds degrees from Dartmouth College and Harvard Business School.
In this episode… What does it really take to succeed in venture capital, where uncertainty is constant, and failure is often part of the process? What separates investors who consistently build strong portfolios from those who don’t?
For Mike Collins, a seasoned venture capitalist and serial entrepreneur, success in venture capital comes from focusing on people over pure ideas and building disciplined, diversified portfolios to manage inevitable risk. He highlights that early-stage investing is less about certainty and more about judgment, trust, and pattern recognition developed over time. A key takeaway is that long-term success stems from striking a balance between conviction and humility and accepting that many investments will fail while a few yield outsized returns. He also emphasizes the value of co-investing and leveraging a global investor community to expand access and insight.
In this episode of the Inspired Insider Podcast, host Dr. Jeremy Weisz sits down with Mike Collins, Founder and CEO of Alumni Ventures, to discuss venture capital, portfolio building, and entrepreneurial lessons. They talk about betting on people over ideas, managing risk through diversification, and lessons from sports and investing. Mike also shares insights on co-investing strategies and democratizing access to venture capital.")
![[Swim Series] Custom Swim Goggles Powered by Innovation With Rasmus Barfred](https://i.ytimg.com/vi/OnWsrf3XkAg/mqdefault.jpg "[Swim Series] Custom Swim Goggles Powered by Innovation With Rasmus Barfred
Rasmus Barfred is the Co-founder of THEMAGIC5, a company redefining athletic gear through custom-fit products powered by 3D scanning and robotic technology. He has helped grow the company into a global brand, securing investment on Shark Tank and expanding its reach worldwide. Building on this technology, he also helped launch Vayu Sleep, which applies custom-fit solutions to CPAP masks for sleep apnea patients. With a background in entrepreneurship, he focuses on scaling innovation across sports and healthcare.
In this episode… What happens when a simple, everyday frustration turns into an opportunity to rethink an entire industry? How do you go from solving one small problem to building technology that reshapes how products are designed and delivered? And what does it take to turn customization into a true competitive advantage?
According to Rasmus Barfred, a visionary entrepreneur and product innovator, solving the issue of poor-fitting swim goggles meant reimagining the entire process through facial scanning and advanced technology. He highlights how starting with a Kickstarter campaign opened the door to diverse user insights, which helped refine both product and software through continuous feedback loops and AI-driven improvements. This approach transformed a niche idea into a scalable system that serves everyone from casual swimmers to elite athletes. He also shares how positioning the business as a tech platform unlocked new growth opportunities and credibility.
In this episode of the Inspired Insider Podcast, host Dr. Jeremy Weisz sits down with Rasmus Barfred to discuss building a tech-driven brand in sports gear. They explore scaling through hardware and software integration, using AI to enhance customer experience, and leveraging partnerships for growth. Rasmus also shares insights on expanding their technology into new industries.")
![[Top Agency Series] Mastering White Label SEO Success With Mark Herre](https://i.ytimg.com/vi/OyTQQ4VtjDE/mqdefault.jpg "[Top Agency Series] Mastering White Label SEO Success With Mark Herre
[Top Agency Series] Mastering White Label SEO Success With Mark Herre")
