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Puzzle

Turpentine

On Tech Finance, host Sasha Orloff brings you inside the office of the CFO - covering major tech finance news including funding announcements, deals, product launches, and emerging players shaping B2B fintech. We break down the week's biggest developments in finance tech and accounting, and explore how finance leaders are putting AI to work.
Tech Finance is brought to you by Puzzle, the modern accounting platform with an AI-first ledger, built for speed, automation, and real time decision making. Learn more: puzzle.io
Tech Finance is part of the Turpentine podcast network. Learn more: turpentine.co

"Turpentine Finance" with Sasha Orloff | Startup Finance, Leadership, CFO Strategy

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:

Creating a competitive process with multiple potential buyers is crucial for maximizing exit value - "if you have one buyer, you have no buyer"

Proper preparation and documentation (clean financials, confidential information memorandum) significantly speeds up the acquisition process and builds buyer confidence

Being transparent about business challenges upfront ("bruises and all") builds trust and allows you to control the narrative around potential objections

--
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

E35: How to Not Be in the Bottom 90% of Acquisitions with Andrew Gazdecki

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:

Accounting profession is facing its most significant period of change, with AI and automation creating both challenges and opportunities for practitioners at all levels.

There's currently a major pipeline issue in accounting - with 75% of CPAs approaching retirement age and not enough new talent entering the field.

Despite technological advances, the fundamental need for trust and human interpretation in accounting remains paramount, suggesting AI will augment rather than replace accountants.

—
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)

E36: From Quill to AI: The Evolution of Accounting with David Hartley, former CIO and CPA

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

E37: Using AI and Humans to Fix Accounting w/ Matt Tait, CEO of Decimal

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

E38: AI-Powered Tax Solutions are Really Here, with Fifteenth Founder Ankur Dahiya

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

E39: The AI Economy: How Agents Will Transact Without Us, with Don Gossen CEO of Nevermined

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

E40: The $500 Domain That Became a Multi-Million Dollar AI Tax Assistant with Kash Ali of TaxGPT

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

E41: Surprising Trends from Deel's Data with Ben Cohen

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

E42: Can AI predict the next unicorn. Crunchbase says yes with 95% accuracy.

This week, Sasha Orloff is joined by Wouter Born, a finance, AI influencer, and General Partner at Born Capital to discuss how AI is reshaping the CFO role and financial tech stack, drawing lessons from Netflix’s rise over Blockbuster, emphasizing innovation, practical AI adoption, and financial storytelling.

--
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/wouterborn/
https://cfooffice.io/

--
X/SOCIAL:
@wouter_born (Wouter)
@sashaorloff (Sasha)

--
TIMESTAMPS:
﻿(00:00) Preview
(00:58) Intro
(01:26) Meet Wouter Born: From founder to AI influencer
(02:39) Wouter entrepreneurial journey
(05:30) Evolution of CFOs in the age of AI
(07:28) Practical AI Tips for CFOs and Founders
(13:01) Future tech stack for CFOs
(17:15) Sponsors: Notion | Puzzle
(18:40) Changing role of CFOs
(21:30) Importance of storytelling in finance
(23:32) Leveraging AI for financial storytelling
(25:54) Building financial tools with AI
(28:51) Future of CFO tech stack
(34:54) Practical advice for AI prompting
(38:39) Connecting with the community
(39:53) Wrap

E43: The CFO's Blockbuster vs Netflix Moment: AI Adoption with Wouter Born

In this episode, Sasha Orloff is joined Alan Imberman, CFO of Wealthfront, about how a client-first philosophy, transparent access, innovative products like S&P 500 Direct Indexing, and strategic use of machine learning have helped Wealthfront grow to $80 billion in assets and 1 million customers, while delivering lower fees, better rates, and sustainable wealth-building strategies.

--
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/alan-imberman-cfa-aab2371/
https://www.wealthfront.com/

--
X/SOCIAL:
@Wealthfront (Wealthfront)
@sashaorloff (Sasha)

--
TIMESTAMPS:
(00:00) Preview
(00:48) Intro
(01:16) Interview with Alan, CFO of Wealthfront
(01:54) Wealthfront's vision and growth
(03:24) Innovative financial products
(04:19) Profitability and business model
(06:03) New product launches and strategies
(15:18) Tax loss harvesting and direct indexing
(17:43) Sponsors: Notion | Puzzle
(19:23) Wealthfront’s tax strategy triumph
(23:13) Bond ladders explained
(28:11) Future of Wealthfront and AI in finance
(33:41) Advice for founders and finance leaders
(36:01) Wrap

E44: From $2B to $80B: Wealthfront CFO Alan Imberman’s 10-Year Journey

In this episode, Sasha Orloff talks with Jean-Denis Greze, Co-founder and CEO of Town, about building an AI-powered tax solution for SMBs, exploring the startup’s origin, the balance between automation and human expertise, strategic market targeting, funding insights, and the transformative potential of AI in tax preparation.

--

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/jeandenisgreze/

https://town.com/

--

X/SOCIAL:

@jgreze (Jean)

@TownTaxCo (Town)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:48) Intro

(01:20) Jean-Denis Greze: The origin story of Town

(02:10) Challenges and opportunities in business tax prep

(03:41) Role of AI in automating tax preparation

(05:50) Market dynamics and constraints in tax services

(15:49) Sponsors: Notion | Puzzle

(17:14) Unique needs of small businesses

(24:38) Future of AI in tax preparation

(26:12) Segmenting the small business market

(27:15) Building trust and scaling AI

(37:14) Exploring AI agents and their potential

(47:21) Fundraising and future plans

(50:57) Wrap

E46: Ex-Plaid CTO on Why Tax is the Ultimate AI Challenge, with Jean-Denis Greze

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