This week, Sasha Orloff sits down with Megh Gautam, Chief Product Officer of Crunchbase, to explore the company’s evolution into an AI-driven intelligence platform, discussing its 95% unicorn prediction accuracy, AI-powered user experiences, pricing challenges, and insights for founders, investors, and job seekers.

--

SPONSORS:

Notion

Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at https://notion.com/startups/puzzle

Puzzle

📈  No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at https://puzzle.io/

--

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/meghbartma/

https://www.crunchbase.com/

--

X/SOCIAL:

@crunchbase

@skyspeak (Megh)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:35) Intro

(01:03) Megh Gautam, Crunchbase's Chief Product Officer

(01:48) Megh’s journey to Crunchbase

(04:26) Transitioning Crunchbase to an AI company

(07:06) Crunchbase's AI and data insights

(09:45) User engagement and product development

(14:58) Sponsors: Notion | Puzzle

(16:22) Forbes article on Crunchbase's AI model

(24:58) Pricing strategies and user experience

(29:33) Future of AI in product management

(35:53) Conclusion and future collaboration

(38:27) Wrap

This week, Sasha Orloff sits down with Ben Cohen, Head of Data from Deel to discuss the company's 2025 Global Hiring Report, covering trends in Gen Z salaries, rising demand for finance roles, global workforce management challenges, domestic hiring shifts, employee termination rates, and the tools Deel provides to support global hires, with an emphasis on trust and asynchronous decision-making for productivity.

--

SPONSORS:

Notion

Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at https://notion.com/startups/puzzle

Puzzle

📈  No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at https://puzzle.io/

--

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/benjamin-cohen-0618308/

https://www.deel.com/

--

X/SOCIAL:

@deel

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:40) Intro

(01:51) Understanding Deal's global hiring report

(02:38) Insights on data utilization

(04:42) Collaboration and data storytelling

(08:23) Generational workforce trends

(08:41) Gen Z's impact on the workforce

(13:59) Sponsors: Notion | Puzzle

(15:39) Global hiring trends and challenges

(19:49) Introduction to global hiring trends

(20:28) Surprising rise of accountants

(22:52) Impact of AI on job market

(25:31) Employee terminations and market trends

(30:01) Tools and insights for global hiring

(33:06) Best practices for a global workforce

(36:33) Data analysis tools

(38:15) Wrap

This week, Sasha Orloff is joined by Kash Ali, Founder and CEO of TaxGPT, who shares how a personal tax issue led to the platform’s creation, its rapid growth after Greg Brockman’s GPT-4 demo, investor interest from Marc Cuban and Jason Calacanis, its shift from a consumer tool to a B2B AI assistant for accountants, its unique advantages over general AI, and his own journey from Pakistan to Silicon Valley, culminating in Y Combinator and a vision for the future of AI-driven tax assistance.

--

SPONSORS:

Notion

Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at https://notion.com/startups/puzzle

Puzzle

📈  No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at https://puzzle.io/

--

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/chkashifali/

https://www.taxgpt.com/

--

X/SOCIAL:

@AskTaxGPT

@ChKashifAli (Kash)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:45) Intro

(01:14) Meet Kash Ali: The Journey Begins

(01:35) Inception of TaxGPT

(02:41) From side project to startup

(04:16) Securing the domain and early success

(07:13) Kash Ali's background and path to Silicon Valley

(13:11) Evolution of TaxGPT

(13:33) Sponsors: Notion | Puzzle

(14:59) TaxGPT's unique value proposition

(19:28) Future of TaxGPT and AI integration

(20:44) Evolution of AI models

(21:48) Enhancing workflows with frontier models

(23:03) Importance of prompting in AI

(28:13) Journey to Y Combinator

(29:55) Fundraising success and future vision

(33:06) Future of accounting and AI

(40:16) Adopting AI solutions in accounting firms

(41:29) Wrap

This week, Sasha Orloff sits down with Donald Gossen, CEO of Nevermined, to explore the future of AI-driven payments, highlighting the company's vision for AI agents with independent accounts and transaction protocols, the challenges of dynamic payment systems, the role of blockchain in security, and Nevermined's journey in enabling decentralized AI-to-AI transactions.

--

SPONSORS:

Notion

Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at https://notion.com/startups/puzzle

Puzzle

📈  No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at https://puzzle.io/

--

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/donald-gossen-40ab96/

https://nevermined.io/

--

X/SOCIAL:

@Nevermined_io

@dongossen (Donald)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:50) Intro

(01:18) Overview of AI-to-AI payments and decentralized finance

(02:34) Vision behind Nevermined

(04:01) Challenges in AI payment systems

(05:34) Nevermined: The PayPal of AI

(06:52) Future of AI commerce

(11:46) Real-world applications and security

(13:54) Sponsors: Notion | Puzzle

(15:17) Security & trust in AI transactions

(19:39) Evolution of AI agents

(27:45) Building Nevermined and fundraising

(32:31) Wrap

This week, Sasha Orloff is joined by Ankur Dahiya, CEO and founder of Fifteenth, a B2B fintech startup using AI to modernize the tax industry, as they discuss his journey from navigating complex stock options at Flexport to transforming CPA services, the challenges of scaling a tax-focused business, the role of AI in automating tax processes, and his vision for more efficient, accessible tax advisory following a successful funding round.

--

SPONSORS:

Notion

Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at https://notion.com/startups/puzzle

Puzzle

📈  No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at https://puzzle.io/

--

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/ankurdahiya/

https://www.fifteenth.com

--

X/SOCIAL:

@sashaorloff (Sasha)

@ankurd (Ankur)

--

TIMESTAMPS:

(00:00) Intro

(01:37) Guest Introduction: Ankur Dahiya

(02:24) Problem with taxes

(03:01) Birth of Fifteenth

(08:33) Combining human expertise with AI

(12:22) Future of AI in tax solutions

(14:40) Sponsors: Notion | Puzzle

(16:03) Managing personal finances

(19:42) Fundraising and building the team

(25:49) Challenges and advice for founders

(27:55) Tax tips for founders and engineers

(33:12) Wrap

In this first episode of Season 2, Sasha Orloff is joined by Matt Tait, CEO of Decimal, to discuss the rise of AI in accounting, Decimal’s recent acquisition of KPMG Spark, and their new strategic partnership with Puzzle. Matt also covers his journey building Decimal, the balance of human expertise in a tech-driven world, and the industry’s future.

--

SPONSORS:

Puzzle

📈  No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at https://puzzle.io/

Found

Found provides small business owners tools to track expenses, calculate taxes, manage cashflow, send invoices and more. Open a Found account for free at https://found.com/econ102

--

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/mtait83/

https://www.decimal.com/

--

X/SOCIAL:

@GoDecimal (Decimal)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Intro

(00:59) Season 2 changes

(01:48) Exciting times in accounting

(03:12) Interview with Matt Tate, CEO of Decimal

(04:22) Rise and fall of Bench

(06:18) Challenges in the accounting industry

(13:03) Founding and vision of Decimal

(16:46) Sponsors: Puzzle | Found

(18:34) Acquisition of KPMG Spark

(23:11) Team collaboration and roadmap insights

(23:45) Scaling with Puzzle's AI native ledger

(24:31) Evaluating technology partnerships

(28:59) Role of trust and accountability in accounting

(29:43) AI's impact on client experience

(31:08) Human interaction vs. full automation

(36:22) Future of AI in accounting

(43:34) Implementing AI tools at scale

(45:14) Wrap

In the final episode of season one, Sasha Orloff is joined by David Hartley, a seasoned CPA with over 30 years of experience, as they explore the evolution of accounting from the 15th century to today's AI-driven landscape and discuss how the profession adapts to technological change while preserving its core value of trust.

—

🙏 Help shape our show by taking our quick listener survey at https://bit.ly/TurpentinePulse.

—

Highlights from the Episode:

—

RECOMMENDED PODCAST:

Check out Modern Relationships, where Erik Torenberg interviews tech power couples and leading thinkers to explore how ambitious people actually make partnerships work. Founders Fund's Delian Asparouhov and researcher Nadia Asparouhova kick off the series with an unfiltered conversation about their relationship evolution.

Apple: https://podcasts.apple.com/us/podcast/id1786227593

Spotify: https://open.spotify.com/show/5hJzs0gDg6lRT6r10mdpVg

YouTube: https://www.youtube.com/@ModernRelationshipsPod

--

SPONSOR:

📝Notion offers powerful workflow and automation templates, perfect for streamlining processes and laying the groundwork for AI-driven automation. With Notion AI, you can search across thousands of documents from various platforms, generating highly relevant analysis and content tailored just for you - try it for free at https://www.notion.com/upstreampod

—

LINKS:

https://www.linkedin.com/in/davehartley/

—

X/SOCIAL:

@sashaorloff (Sasha)

In this episode, Sasha Orloff is joined by Andrew Gazdecki, founder of Acquire.com, who shares his expertise on successfully selling companies, maximizing exit value, and key lessons from his own acquisition experiences, with over $500 million in closed deals.

—

🙏 Help shape our show by taking our quick listener survey at https://bit.ly/TurpentinePulse.

—

Highlights from the Episode:

--

RECOMMENDED PODCAST:

Check out Modern Relationships, where Erik Torenberg interviews tech power couples and leading thinkers to explore how ambitious people actually make partnerships work. Founders Fund's Delian Asparouhov and researcher Nadia Asparouhova kick off the series with an unfiltered conversation about their relationship evolution.

Apple: https://podcasts.apple.com/us/podcast/id1786227593

Spotify: https://open.spotify.com/show/5hJzs0gDg6lRT6r10mdpVg

YouTube: https://www.youtube.com/@ModernRelationshipsPod

—

SPONSOR:

📝Notion offers powerful workflow and automation templates, perfect for streamlining processes and laying the groundwork for AI-driven automation. With Notion AI, you can search across thousands of documents from various platforms, generating highly relevant analysis and content tailored just for you - try it for free at https://www.notion.com/upstreampod

—

LINKS:

Acquire: https://acquire.com/

https://www.linkedin.com/in/agazdecki/

—

X/SOCIAL:

@acquiredotcom (Acquire)

@agazdecki (Andrew)

@sashaorloff (Sasha)

—

TIMESTAMPS:

(00:00) Intro

(02:10) Personal lessons from selling Business Apps

(03:50) Building Acquire.com from personal experience

(06:49) First acquisition story with ESW Capital

(09:28) Negotiating terms and tax considerations

(12:20) Story of Altcoin acquisition

(13:53) Sponsor: Notion

(15:15) Experience at Spiff and path to Acquire.com

(18:35) Maximizing exit value strategies

(25:47) Process of listing on Acquire.com

(27:36) Types of buyers and deal sizes

(29:34) Success stories and notable deals

(32:57) Future plans for Acquire.com

(34:04) Wrap

This week, Sasha Orloff sits down with JustPaid founders Daniel Kivatinos, a successful YC founder behind the first iPad medical records company, and Anelya Grant, a Kazakhstan immigrant who built an accounting practice for YC startups, about how their unique backgrounds inspired them to tackle the critical challenge of accounts receivable automation with an AI-powered platform. For full show notes, visit: https://highlightai.com/share/309bb91f-34ee-4052-88e5-28718a9101da

—

🙏 Help shape our show by taking our quick listener survey at https://bit.ly/TurpentinePulse.

—

SPONSOR:

📝Notion offers powerful workflow and automation templates, perfect for streamlining processes and laying the groundwork for AI-driven automation. With Notion AI, you can search across thousands of documents from various platforms, generating highly relevant analysis and content tailored just for you - try it for free at https://www.notion.com/upstreampod

—

LINKS:

Streamlining Accounts Receivable: Transforming an Overlooked Cornerstone of Business Operations: https://www.justpaid.ai/blog/streamlining-accounts-receivable

JustPaid: https://www.justpaid.ai

https://www.linkedin.com/in/kivatinos/

https://www.linkedin.com/in/anelya/

—

X/SOCIAL:

@getjustpaid (JustPaid)

@danielkivatinos (Daniel)

@sashaorloff (Sasha)

Today, we’re sharing a special episode from our friends at the Webby Awards-honored CRAFTED. podcast. In this conversation, Dan Blumberg interviews growth expert, SYSTM founder, and former PayPal leader Matt Lerner about his book 'Growth Levers,' offering actionable strategies for startups to identify the 10% of efforts that drive 90% of growth. They discuss common startup pitfalls, the mindset shift to customer-centric thinking, JTBD-style interviewing, and the importance of rapid experimentation. For full show notes, visit: https://highlightai.com/share/af10e152-f30a-403e-805f-d234eb40109a

—

🙏 Help shape our show by taking our quick listener survey at https://bit.ly/TurpentinePulse.

—

Check out Dan Blumberg's CRAFTED. where he interviews founders of high growth startups, including from Lattice, Gusto, Moov, Monte Carlo, Customer.io and our own Sasha Orloff!

Apple: https://podcasts.apple.com/us/podcast/crafted-the-tech-podcast-for-founders-makers/id1649355311

Spotify: https://open.spotify.com/show/3xtU2V1jRP89aI1ULRN2GI?si=b5753bd5be14494c

—

SPONSOR:

📝Notion offers powerful workflow and automation templates, perfect for streamlining processes and laying the groundwork for AI-driven automation. With Notion AI, you can search across thousands of documents from various platforms, generating highly relevant analysis and content tailored just for you - try it for free at https://www.notion.com/upstreampod

—

LINKS:

Matt Lerner's company: https://www.systm.co/

CRAFTED. podcast: https://crafted.fm

Growth Levers: https://www.amazon.com/dp/173842622X

—

LinkedIn:

Matt Lerner https://www.linkedin.com/in/matthewlerner/

Dan Blumberg https://www.linkedin.com/in/dblums/

Sasha Orloff https://www.linkedin.com/in/sashaorloff/