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Very True by Verissimo
Alex
12 episodes
1 week ago
Brought to you by Verissimo Ventures, The Very True Podcast features candid startup insights and conversations with early-stage founders, operators, and investors shaping the future of tech. From behind-the-scenes startup stories to hard-earned lessons on fundraising, scaling, and staying resilient, each episode offers a window into what it really takes to build something bold.
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Entrepreneurship
Business,
Investing
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All content for Very True by Verissimo is the property of Alex and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
Brought to you by Verissimo Ventures, The Very True Podcast features candid startup insights and conversations with early-stage founders, operators, and investors shaping the future of tech. From behind-the-scenes startup stories to hard-earned lessons on fundraising, scaling, and staying resilient, each episode offers a window into what it really takes to build something bold.
Show more...
Entrepreneurship
Business,
Investing
Episodes (12/12)
Very True by Verissimo
What is your startup actually worth? Probably a lot less than you think...

Startup valuations get discussed like baseball player stats, but they're much less well-defined. When primary capital is at stake, the calculations are different. Happy to share here some of those nuances and how founders and investors should approach startup valuations. 

Check out the fundraising framework here https://verissimo.vc/resources-for-founders

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2 weeks ago
30 minutes

Very True by Verissimo
Why Companies Fail and Why I Started This Podcast

Startup success stories are usually stories of unique circumstances and personalities - each one like a snowflake. 
Startup failures fit into a handful of categories. That's what we're talking about today. 
Companies with high potential that avoid the pitfalls are the ones that find success - either small, medium or large. But if you can't avoid the unforced errors, you haven't even given yourself a chance! 

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2 weeks ago
48 minutes

Very True by Verissimo
Software as a Service or Service as Software? How AI changes the game for data tools with Gabi Steele, CEO of Preql

We are amidst yet another swing of the pendulum when it comes to the software vs. services debate. Is it possible to have high value, low touch software? Are we better off just offering high end consulting services using custom tools? 
I am excited to share my conversation with Gabi Steele, CEO of Preql who has done both as she discusses the opportunities and challenges presented by the current array of AI tools in the data space. 

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3 weeks ago
37 minutes

Very True by Verissimo
Revenue? If you have Revenue, people will ask how much and it will never be enough!

Legendary Silicon Valley episode illustrates this question so well, I just have to leave it here: https://www.youtube.com/watch?v=BzAdXyPYKQo
(Contains expletives). 
How are startups valued pre-revenue? Is it better to stay in that zone as long as possible? 

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3 weeks ago
11 minutes

Very True by Verissimo
PLG & User Activation with Yaakov Carno of Valubyl

Happy to share a discussion with Yaakov Carno, founder of Valubyl, which is a leading PLG consulting agency focused on the specific bottle neck of user activation. He shares stories from the trenches of working with dozens of companies and helping navigate their product and growth optimization. 
Follow Yaakov on social media to get his latest tips and ideas on how to maximize user activation: https://www.linkedin.com/in/yaakov-carno/
https://www.valubyl.com/

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3 weeks ago
43 minutes

Very True by Verissimo
Is ARR Dead? Wait, What Even is ARR?

Is ARR dead with the advent of AI companies? Do we even know what ARR is? Why does it matter? Why is everyone so confused about it? 
Nerding out on tech finance finance, yet again. 

related posts: 
https://docs.google.com/presentation/d/1CUxLWt16Ky5eulArPm4cTSubkZWQ8rkBDPVZWHwJxUU/edit
https://alexoppenheimer.substack.com/p/inventing-arr
https://alexoppenheimer.substack.com/p/calculus-in-saas  

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1 month ago
26 minutes

Very True by Verissimo
Bifurcation of an Asset Class - October Verissimo Monthly

Want to be the next $50Bn startup? Maybe... maybe not. 
How the economics change the reality on the ground, even at the early stage. 
Subscribe to our monthly updates here: https://verissimo.substack.com/

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1 month ago
24 minutes

Very True by Verissimo
How to be Wrong in Early Stage Venture

Today I discuss the painful reality of venture: investors are wrong a lot. They lose money. But are all mistakes created equal? Or is there a better way to be wrong. I dive in here to review a market take that I had ~3 years ago to see how things have developed in the market and in my one portfolio when it comes to the less fortunate situations in early-stage investing. 

As always, feel free to reach out with feedback or questions. 

Original piece here: https://alexoppenheimer.substack.com/p/expensive-options-and-losing-big

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1 month ago
35 minutes

Very True by Verissimo
The Financial Operations Flow - Comprehensive Review

In this episode, I break down the Financial Operations Flow. This is targeted towards CEOs (CFOs can also listen if they want), to help business leaders better understand how to quantify the resource allocation they need to be doing all the time. 
Every business needs a digital twin... Good news: for most of them, Excel is a sufficient tool to have a huge impact - it just needs to be used correctly. 

Original post here: https://alexoppenheimer.substack.com/p/the-finops-flow

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1 month ago
22 minutes

Very True by Verissimo
Engineering Architecture & Scaling Teams - It's All About Everything Series

🎧 New on the Podcast: The Evolving Role of a CTO

This episode dives deep into how the CTO role evolves—from early-stage coding to scaling teams, making strategic decisions, and integrating AI without losing your technical edge.

Featuring:

  • Michael Stoppelman, Former SVP Engineering at Yelp
  • Gustav Rydstedt, Chief Architect at Chegg, former CTO & Co-founder of Verbling
  • Moderated by Nitay Joffe, CTO & Co-founder of ActionIQ, Partner at Verissimo Ventures

💡 Key themes explored:

  • Staying hands-on as a technical leader
  • Building process without bureaucracy
  • Leading with both conviction and emotional intelligence
  • Embracing AI while maintaining core engineering skills 
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5 months ago
59 minutes

Very True by Verissimo
Understanding Your Legal Docs - It's All About Everything Series

🎧 New on the Podcast: Legal Essentials for Founders

In this episode of the It’s All About Everything series, we dive into the legal foundations every founder should get right from day one. From filing your 83(b) on time to guiding your legal team through negotiations and keeping a clean cap table, our expert panel breaks down the critical legal decisions that can make—or break—your startup's future.

Whether you're raising your first round or scaling fast, this conversation will help you avoid costly legal pitfalls and build with confidence.

Featuring:

  • Mordechai Hartman – Principal at Hartman Venture Advisors PLLC
  • Josh Eisenson – Partner at Goodwin
  • Maria Kuehn – Head of Legal at ActionIQ
  • Moderated by Alex Oppenheimer – General Partner at Verissimo Ventures
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5 months ago
56 minutes

Very True by Verissimo
Tax Strategies and Wealth Management- It's All About Everything Series

🎧 New on the Podcast: Tax Strategies and Wealth Management

In this episode of the It’s All About Everything series, we break down the financial essentials every founder should understand before—and after—a liquidity event. From QSBS and 83(b) elections to trust structures and the family office mindset, our expert panel shares real-world strategies to help you protect your upside and build long-term financial stability.

Whether you're preparing for an exit or just getting started, this episode will help you make smarter, more informed financial decisions.

Featuring:

  • Todd Saunders – (Moderator) CEO at Broadlume (recently exited)
  • Tres Evans – Managing Director & Private Wealth Advisor at Morgan Stanley
  • Robbie Shattuck – CEO & Founder of Athos Private Wealth
  • Aaron Bedrick – CEO & Founder of Symphony Strategies
  • Max Sabert – Private Wealth Advisor at UBS
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5 months ago
1 hour 2 minutes

Very True by Verissimo
Brought to you by Verissimo Ventures, The Very True Podcast features candid startup insights and conversations with early-stage founders, operators, and investors shaping the future of tech. From behind-the-scenes startup stories to hard-earned lessons on fundraising, scaling, and staying resilient, each episode offers a window into what it really takes to build something bold.