Uncharted Podcast

On this episode of the Uncharted podcast, we're joined by Phil Carr, a seasoned tech entrepreneur. Phil dives into his journey from building and exiting the successful fitness platform, My PT Hub, to his current venture, Upzelo. He shares invaluable insights on his strategic pivot from SaaS retention to e-commerce loyalty, the unique challenges of being a second-time founder, and his take on AI's evolving role in the tech landscape. Tune in for candid lessons on self-awareness, raising capital, and navigating market shifts.

How do you build partnerships that actually drive revenue—not just relationships? In this episode, Billy Robbins joins to break down the evolution of partnerships, the rise of marketplaces like AWS, and how to create real value through strategic collaboration. Whether you're building your first BD function or scaling with hyperscalers, this one’s packed with hard-earned insight.

In this candid and heartfelt episode, we dive deep into a personal journey of resilience, growth, and authentic connection. Poya shares their experience growing up as an immigrant in America, navigating career transitions from politics to sales, and building a successful consulting practice based on genuine relationships. They reveal how childhood insecurities transformed into a passion for empowering others, the importance of learning through experience, and why they now measure success by happiness rather than income. From overcoming professional setbacks to finding purpose in helping others succeed, this conversation explores how vulnerability and loyalty have shaped their approach to business and life. Discover powerful insights about perseverance, authentic leadership, and why sometimes the best path forward is simply to "step the fricking up" when facing life's challenges.

Amir Orad shares how he scaled three companies to over $150M, navigated crises like 9/11 and the financial crash, and built winning teams through reinvention, resilience, and relentless focus. A masterclass in scaling SaaS through chaos.

In this episode of Uncharted, host Poya shares invaluable insights from his recent keynote at SaaStanak conference in Croatia. Drawing from his personal journey as an immigrant and his experience helping European startups succeed in the US, Poya breaks down the most common pitfalls founders face when expanding internationally. From the importance of founders owning the sales process to building genuine relationships instead of transactional ones, this episode delivers practical advice on how to navigate the American business landscape. Whether you're considering US expansion or simply looking to improve your sales approach, you'll learn why being opinionated matters, how to add value in follow-ups, and why documentation is critical for scaling success. Don't miss these battle-tested strategies from someone who has helped multiple companies achieve their American dream.

Our speaker this week is Jonathan Festejo. He is the CEO and co-founder of Salesbricks, where he is dedicated to making software easier to buy. He leads the company’s vision, strategy, and long-term growth. With firsthand experience in the challenges of selling software in today’s digital world, Jonathan is focused on making software more accessible through simple, click-to-purchase solutions. Before founding Salesbricks, he managed go-to-market operations at several companies backed by Andreessen Horowitz (a16z) and oversaw more than $2 billion in software sales contracts.

Arthur Bigeard shares his journey from a passion project to a thriving business, turning a side hustle into a full-time venture. He discusses the long-term mindset behind building scalable software, the lessons learned from working at Morgan Stanley, and the strategic decisions that helped shape g.v, a graph database client. Tune in for insights on entrepreneurship, tech evolution, and making the leap into the unknown!

About our speaker:

Arthur Bigeard is the founder at gdotv, a universal, plug-and-play graph database client to simplify & accelerate the day-to-day tasks of graph database users. He started this project following a 10 years long cyber security career, specialising in Identity & Access Management and cryptographic solutions.

In this episode of The Uncharted Podcast, host Poya Osgouei sits down with Lucas Lovell, VP of Product at Paddle, to discuss his journey from law school to founding a SaaS company and ultimately transitioning into a leadership role at a fast-growing scale-up. Lucas shares insights on navigating the shift from founder to operator, the value of cross-functional relationships, and the importance of customer empathy in product development. He also offers valuable advice for early-career professionals on prioritizing learning and leveraging strengths to create a lasting impact.

Tune in for a deep dive into leadership, adaptability, and growth in the tech world!

This week's guest is Ryan Fox-Tyler who is currently building Hypermode, an AI development platform that makes it easy to build intelligent apps and knowledge graphs. Prior, he led product at Astronomer (the data orchestration company) and spent a decade in various roles at Manulife/John Hancock.

In this episode ofUncharted, we explore the power of collaboration in sales and leadership. Our guest shares insights on how a strong partnership mindset—rather than a zero-sum approach—can drive bigger wins, foster trust, and create lasting professional relationships. From splitting deals to scaling success, we discuss the key ingredients that make teamwork thrive and how these lessons apply to leadership, decision-making, and career growth. Tune in for stories of mutual support, business insights, and advice on building relationships that stand the test of time.

Poya Osgouei, the founder of Event Sponsors, shares insights on the evolution of B2B tech events, the art of relationship building, and how to create valuable networking experiences.

From his journey starting at Oracle to becoming an events expert, Poya discusses the shift toward niche communities, measuring event ROI, and strategies for meaningful professional connections.

This episode of the Uncharted podcast features Phil Carr, a tech entrepreneur discussing his journey from founding and exiting My PT Hub (a successful B2B2C fitness platform) to his current venture, Upzelo. Phil shares insights about his recent pivot from a SaaS retention product to an e-commerce loyalty platform, discussing the challenges of second-time entrepreneurship, knowing when to pivot, and his perspective on AI's impact on technology. The conversation covers valuable lessons about self-awareness in entrepreneurship, raising capital, and adapting to changing market conditions.

This episode is brought to you by Netsuite, learn more at Netsuite.com

In this episode of Uncharted, Poya kicks off 2025 with an insightful conversation with Haroon, CEO of Autoblocks AI, a company pioneering tools to ensure the safe deployment of AI. Haroon shares his journey from being an ML engineer to co-founding Autoblocks, highlighting his passion for building trust in AI systems. The discussion explores the AI industry's rapid evolution, the challenges startups face in standing out, and the strategic importance of solving immediate customer pain points. Tune in to hear Haroon's grounded perspective on navigating the hype around AI, his thoughts on the battle between AI-native startups and industry incumbents, and advice for those entering the space.

About our guest:

Haroon is the Co-Founder & CEO at Autoblocks AI, one of the first-ever AI evaluation platforms. 

He is also the host of the Building With AI podcast, where he interviews & distills best practices from top AI product teams at companies like OpenAI, Intercom, and Retool. 

Haroon previously founded one of the top AI literacy nonprofits in the US, AI For Anyone, and is passionate about democratizing knowledge about AI.

Brought to you with support from Netsuite. Learn more at Netsuite.com/scale

This week is a special episode as we dive into the five lessons from this year's Uncharted Podcast!

Discover insights that can transform your perspective, boost your growth, and inspire your journey. Tune in for valuable takeaways and reflections that you won't want to miss!

This week's guest is Varun Sharma, CEO and co-founder of Enterpret.

Varun's journey to founding Enterpret began at Amplitude, where, as employee 15, he helped scale product analytics for startups to Fortune 500s. During this time, Varun identified a major gap: product teams knew what was happening with their data but not the why. The solution? Insights were buried in unstructured feedback—messy, inconsistent, and impossible to scale. Today, Varun and his team at Enterpret help companies like Canva, Notion, Vimeo, and Strava turn feedback into actionable insights, empowering teams to drive growth and build products users love.

About this week's guest: Jeremy is an entrepreneur whose goal is to create products that positively impact people's lives. He caught the startup bug 18 years ago and has been building and growing products ever since. His first startup journey concluded when his team was acquired by Facebook, where he went on to spend nine years in growth and product roles. Now, Jeremy is focused on building Sidebar, a platform with a mission to connect leaders and catalyze their extraordinary success. Outside of work, he enjoys spending time with family and friends in the mountains, skiing and trail running, or at the beach, learning how to surf.

This week's a re-purposed episode from a popular episode few years back to celebrate a popular episode with Airbase CEO which recently exited to Paylocity. The guest is Thejo Kote, CEO of Airbase.  His first startup, Automatic, was acquired by Sirius XM for $100m and Airbase recently announced they are being acquired by Paylocity for $325 Million.

This week's episode is brought to you with support from Netsuite

Tido was an early engineering leader at Facebook, Dropbox, and Chief Product Officer @ Segment from early days through its acquisition by Twilio. He now is Co-Founder @ Koala, which is an end-to-end pipeline generation platform used by thousands of Sales teams.

Karim Atiyeh is the co-founder and CTO of Ramp, a finance automation platform that helps businesses spend less time and money. Founded in 2019, Ramp powers the fastest-growing corporate card in America and enables billions of dollars of purchases each year on the heels of nearly 10x year-over-year growth. Valued at $8.1 billion two years after launch, Ramp has raised hundreds of millions in equity from backers including Founders Fund, General Catalyst, Redpoint Ventures, Thrive Capital, D1 Capital Partners, Spark Capital, Coatue Management, Iconiq, Goldman Sachs, and Stripe. A Lebanese entrepreneur, Karim previously built and sold Y Combinator-backed Paribus to Capital One in 2016.

This episode is brought to you with the support of Netsuite, download their guide at netsuite.com/scale

Andrew Davies is the CMO of Paddle, a payments infrastructure platform for high-growth SaaS companies serving over 3000 customers. He has more than 20 years of experience in start-ups ranging from leading global demand, advisory and consultancy, and even teaching.

Tony Barbagallo is the VP of Marketing at DuploCloud, a company that automates the most tedious tasks of DevOps. Prior to DuploCloud, Tony served as the CEO of Caringo where he was previously spearheading marketing. Prior to that, he held a variety of roles across startups and large enterprises in product management, sales, marketing and engineering. A graduate of Syracuse University, Tony currently resides in the Bay Area.

About our speaker:

Shensi Ding is the co-founder and CEO of Merge, a company that offers a unified API to add hundreds of integrations to your product. Prior to founding Merge, Shensi served as the Chief of Staff at Expanse (acquired by Palo Alto Networks) and worked in investment banking roles at Credit Suisse and Silver Lake. A graduate of Columbia University, Shensi currently resides in and works out of New York City.

Our speaker this week is Sean Ericson, where we discussed the following, the founder of Abloom GTM, a sales development advisory firm that architects SDR and RevOps motions. Before Abloom, he provided foundational consulting services for 30+ startups like Clearbit, ConductorOne, Semgrep and Dolby.io as a Partner at InsideScale, and was a founding SDR at Talkdesk. Sean holds a Master's in International Development from the London School of Economics and is currently building a SaaS product for nurses.

This Week's Episode is Brought to you with Netsuite. Get a personalized demo at Netsuite.com/Scale - that is netsuite.cm slash scale.

This week's guest is James Evans, the co-founder and CEO of CommandBar, a user assistance software company that powers chat and proactive help interfaces for hundreds of software businesses and millions of end users. Before CommandBar, he worked in private equity investing at Bain Capital and studied CS at Princeton.

Here’s a summary of the key points from the interview with James Evans on the Uncharted podcast:

1. Introduction & Background:

   • James Evans is the founder of Command Bar, and he shares an interesting fact about his past: he played bass in a heavy metal band in high school.
   • He has an impressive educational and professional background, including attending Princeton and working at Bain before founding his company.

2. Family and Personal Drive:

   • James mentions his parents are immigrants (his mother from Iran and his father from the UK) and both are business school professors.
   • He didn’t feel typical immigrant pressure to succeed but did feel a self-imposed pressure to do something meaningful as a founder, influenced by his upbringing and his parents' careers.

3. Path to Entrepreneurship:

   • James’s first job was in finance, but he always aspired to be a founder. His first startup was an early-stage crypto company, which didn’t succeed, leading him to start Command Bar.
   • He emphasizes the importance of choosing to work on something meaningful rather than starting a company for the sake of it.

4. Challenges and Pivots:

   • James talks about the challenges of knowing when to pivot or move on from a project. He shares his experience pivoting from his first startup to Command Bar and later adjusting Command Bar’s strategy post-Series A funding.
   • He advises founders to be adaptable and willing to reassess their strategies, even after raising funds.

5. Mindset and Resilience:

   • James discusses the importance of resilience and the inevitability of facing highs and lows as a founder. He notes that experiences that seem devastating in the moment often feel less significant over time.
   • He emphasizes that the only fatal mistakes in a startup are giving up or running out of money.

6. Command Bar’s Market Position:

   • Command Bar operates in two categories: B2B chatbots and digital adoption tools, and they are exploring the creation of a new category called "user-assisted software."
   • James highlights the balance between creating new categories and fitting into existing markets for buyer recognition.

7. Sales and Enablement:

   • The company focuses on empathy and genuine curiosity in sales, prioritizing understanding customers’ problems over simply selling products.
   • James discusses the challenges of sales enablement in a multi-product context and the importance of storytelling in sales.

8. Advice to Young Entrepreneurs:

   • James advises making decisions quickly and not overthinking minor details. He believes the best action is often to make a decision and move on rather than getting stuck in analysis.

9. Conclusion:

   • The host and James discuss the importance of taking decisive action and the value of having conversations with more experienced entrepreneurs to avoid getting stuck in decision-making

On this episode we delve into the inspiring journey of Tim Schumacher, the CEO and co-founder of SaaS Group.

Tim shares his entrepreneurial adventures, from coding games in his teens to scaling successful companies and becoming a key player in SaaS. Discover his insights on making acquisitions founder-friendly, the importance of long-term vision, and his passion for climate tech. This conversation is filled with valuable lessons for anyone interested in entrepreneurship, investment, and sustainable business practices.

This Week's Episode is Jim Yu, Founder and Chairman of BridgeEdge.

Jim is the founder and exec chair of BrightEdge. As CEO of BrightEdge, Jim helped create a whole new category in digital marketing software and built BrightEdge into the enterprise market leader with $100M+ in revenue, profitable, and 500 employees. It is used by 57% of Fortune 100 companies and nine out of the top ten international digital agencies. BrightEdge is backed by Altos Ventures, Battery Ventures, Intel, and Insight Partners.
As the global leader in enterprise organic search, content, and digital automation, it empowers marketers to transform online content into business results, such as traffic, conversions, and revenue. It is powered by a sophisticated deep-learning engine and contains the industry's most extensive data set. Its all-in-one platform provides vital market insights and business intelligence based on secure, compliant, and robust sets of first-party, real-time, and historical data.
Jim is a founder, digital marketing expert, and speaks at conferences such as Share, Dreamforce, Adobe Summit, as well as Search Engine Expo and Search Engine Strategies worldwide. In addition, Jim is an industry pundit with featured columns in Entrepreneur, Fortune, ClickZ, Search Engine Land and Huffington Post. Jim is widely recognized as the driving force behind enterprise content performance marketing technology, having built the largest and most widely adopted platform which is in use by over 20,000 digital marketing professionals across 8,400 brands around the globe.
Jim holds an MBA from Stanford University, a Master's of Engineering from the University of Virginia, and a Bachelor's of Science in Computer Science from the University of South Dakota.

Sid is the Head of Studio at Forum VC, a venture studio with a goal of building 8 AI companies per year.

Prior to joining Forum VC, Sid started Broca, an AI software that generates ad copy and other forms of marketing content. He has also helped dozens of SAAS companies with their growth. Some companies he has worked with include Thinkific, LemonStand, Gorgias, Plato, Typeform, and ClickUp

This episode is brought to you with the support of Oracle Netsuite, learn more at netsuite.com/uncharted

We're excited to re-release one of our earliest and most insightful episodes from 2020, featuring Greg Sands, Founder and Managing Partner of . In just 15 minutes, Greg shares his journey from skating on frozen Minneapolis lakes to shaping the future of early-stage investing.

Discover the principles that guide his investment strategy, and the art of being an exceptional investor. Greg also dives into the dynamics of early-stage enterprise SaaS investments and the evolving landscape of venture capital.

Whether you're an aspiring entrepreneur, an investor, or just curious about the inner workings of venture capital, this episode is packed with timeless wisdom and practical advice.

Join us as Greg Sands takes us through his career, offering invaluable lessons on leadership, curiosity, and the drive needed to succeed in the fast-paced world of startups. Enjoy the episode and thank you for your continued support!

This week's episode features a repurposed interview where Federico Ramallo interviewed Poya Osgouei on the IrregEx Podcast. Federico's qustions were put together using an AI speaker. In this episode, Poya dives deep into various topics, including his experiences growing up as an immigrant in the United States, what he's learned over the years as a startup advisor and his approaching to sales. This episode is brought to you with the support of our sponsor, Oracle Netsuite.

This Week's Guest is Kevin Mulrane.

Kevin Mulrane jumped onto Sales Operations Demystified to share his thoughts on the blurring of sales leadership and sales operations, why sales reps need to become the CEO of their own business and why you should "Win what is winnable".

This week's guest on Uncharted Podcast with Poya Osgouei is Fabian Veit, the CEO at Make. Fabian joined the leadership team of Make in 2020 after the business was acquired by Celonis, a leading process mining platform and execution management software. Before Make, Fabian held various roles at Celonis, from Data Scientist to VP Operations and People COO, spearheading the organization's growth operations and team development from a small team of just twenty individuals to a thriving organization with over 1,000 employees

Amir Orad, a seasoned CEO/entrepreneur in AI/analytics, Cyber, and FinTech, has a proven track record of scaling tech companies, including Sisense, Actimize, and Cyota, achieving 9-figure revenues, profitability, and market leadership.

As CEO & Chairman of Sisense, revenue grew 17X over eight years to $150M, transitioning to native cloud SaaS and achieving profitability. Sisense serves thousands of customers, recognized as a Visionary/Leader by Gartner, G2 Crowd, and Forrester.

Previously, as CEO of NICE Actimize, revenue grew 10x to $200M with over 25% operating income, transitioning to a SaaS/Subscription model. Orad co-founded Cyota, growing it to $100M in bookings in six years before its acquisition by RSA Security.

With expertise in mergers and acquisitions, Orad successfully integrated four acquisitions into his companies over 20 years. He's also chaired/boarded companies like AnyWord, Yotpo, SecuriThings, Ava, and BillGuard.

Starting his career as a techie, Orad holds patents and is recognized as an industry thought leader in publications like the Wall Street Journal and CNBC. Based in New York, he holds an MBA from Columbia University and a B.Sc in Computer Science and Management from Tel Aviv University, receiving accolades like EY Entrepreneur of the Year and Goldman Sachs' 100 Most Intriguing Entrepreneurs.

This week's episode is brought to you with support from DuploCloud.

This week's speaker is Aaron McReynolds. With over nine years of experience in sales and sales management, Aaron is currently the Co-Founder and CEO of Alysio, a software company that helps sales teams optimize their performance and efficiency via AI. Aaron has a proven track record of leading and growing sales teams in various markets, such as enterprise, corporate, and international. He has also successfully sold and managed accounts for some of the leading software companies in the industry, such as Lacework, Okta, and Qualtrics. Aaron began his career at Goldman Sachs within the Asset Management Division. He is a Brigham Young University alumni.

This week, we have an engaging discussion with Pete Ryan, co-founder of Hifive. While SaaS fundamentals like MVPs and growth are on the table, the real focus here is the founder's mindset—a make-or-break factor on the path from zero to one. Take a listen to uncover the valuable insights that can set your startup on the right track.

Peter Ryan, the co-founder of Hifive (formerly CoSell), has a wealth of experience in SaaS and B2B sales. His journey is a testament to the transformation possible in the startup realm, making him a valuable figure for SaaS founders and investors.

This week's episode features Ashley Montgomery, who runs Montgomery Entertainment and is experienced in event productions, discuss event partnerships with Poya Osgouei.

This week's guest is Brent Chudoba.

Brent lives in Charleston, SC and has been the CEO of Biteable since February 2020. Prior to Biteable, he was COO at Calendly, COO/CFO at Thrive Global, COO at PicMonkey, Board Director at Schoology, and CRO at SurveyMonkey where he joined at as an early employee. Before his operating career, Brent was an investor at Spectrum Equity investors and an investment banking and hedge fund analyst. Brent attended Columbia University. When he’s not working on software businesses, he spends his time chasing around his three young boys on the beach or the soccer field.