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Artwork for "Tech Finance" with Sasha Orloff: B2B Fintech

"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech

Puzzle, Turpentine
Venture Capital
Mergers and Acquisitions
Accounting
Artificial Intelligence
Entrepreneurship
Fintech
Tax Compliance
AI Innovations
Startups
AI In Accounting
Accounting Software
ERP
Corporate Development
AI In Finance
Silicon Valley Bank
Startup Funding
Product Development
Taxgpt
Y Combinator
Openai

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 acc... more

PublishesTwice monthlyEpisodes67Founded3 years ago
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ManagementEntrepreneurshipBusiness

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Artwork for "Tech Finance" with Sasha Orloff: B2B Fintech

Latest Episodes

In this episode, Sasha Orloff sits down with Luke Frye, founder of LukeFrye.co, to trace his decade-long journey through foundational fintech pioneers like Bench and Pilot and explore how AI is shifting the accountant's role from manual data entry to... more

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In this episode, Sasha Orloff speaks with Greg Capitolo, Co-founder and Partner at Attivo Partner, to discuss how fractional finance teams are transitioning from manual bookkeeping to AI-driven advisory roles, emphasizing the shift toward "real-time ... more

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In this episode, Sasha Orloff speaks with Tarek Alaruri, CEO and Co-founder of Stuut, about raising a Series A from Andreessen Horowitz to build an AI-powered accounts receivable platform that automates the entire AR function—from credit and collecti... more

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In this episode, Sasha Orloff sits down with Sam Ross, co-founder and CEO of Numeral and former product leader at Teespring and Airbnb, about raising Series B funding from Mayfield (following Benchmark's Series A and Uncork's seed) to build what he c... more

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Recent Guests

Luke Frye
CPA, former Bench early employee, and founder of consulting practice; has worked at Bench, Pilot, Rivet, and Puzzle
Consulting practice; former Bench employee; Puzzle alumnus
Episode: E67: Navigating the Era of "AI Slop" in Accounting with Luke Frye
Greg Capitolo
Partner and Co-founder, Attivo
Attivo
Episode: E66: Engineering the Modern Accounting Firm with Greg Capitolo of Attivo Partners
Tarek Alaruri
CEO of Stuut
Stuut
Episode: E65: a16z-backed Stuut CEO Tarek Alaruri on Why Legacy AR Software Failed and How AI Fixes It
Sam Ross
Founder and CEO of Numeral, previously worked at Teespring and Airbnb.
Numeral
Episode: E64: Numeral CEO Sam Ross: Why I Abandoned My Profitable Business to Raise $50M for Something "Boring"
Usman Gul
CEO of Metal and serial founder focused on AI-driven fundraising solutions.
Metal
Episode: E63: Reverse Engineering Venture Capital with Metal's Usman Gul
Renato Villanueva
Founder of Parallel and former FP&A at Divvy
Parallel
Episode: E62: From Divvy FP&A to Parallel Founder: How Renato Villanueva Built the Tool Finance Actually Wants
Yogi Goel
Founder and CEO of Maxima
Maxima
Episode: E61: Maxima's $41M Mission: Automating Enterprise Accounting Close with AI
Dan Westgarth
COO of Deel
Deel
Episode: E60: Deel's COO on Scaling to $17.3B Valuation (and Where They Go From Here)
Nick Abouzeid
Co-founder and CEO of Rivet, a modern tax and accounting firm.
Rivet
Episode: E59: Why AI Tax Tools Fail the QSBS Test, with Nick Abouzeid of Rivet

Host

Sasha Orloff
CEO of Puzzle; host of Tech Finance, focusing on the intersection of finance, technology, and AI-enabled accounting. Brings executive-level CFO insights and a deep network in the fintech space.

Reviews

5.0 out of 5 stars from 116 ratings
  • I have listened to every single one

    So I might be biased, but I am so excited about this. These are really fun stories that are usually told privately in board rooms or over beers, now for everyone to get to hear.

    Apple Podcasts
    5
    Mover415
    United States2 years ago
  • A true Master Class for all aspiring CFOs

    Each interview selects a key topic or subject area that any CFO will have to deal with. These are conversations that convey key learnings from industry veterans.

    CJ has a great interview style where he gives each guest the space to discuss each topic in depth.

    I often listen to each session multiple times given the volume of wisdom and experience from each conversation.

    Apple Podcasts
    5
    RobMitch78
    United States2 years ago
  • Learn something new every time!

    I’ve been involved with SaaS businesses for over 10 years and amazed by how much I learn every podcast!

    Apple Podcasts
    5
    Colby28
    United States2 years ago
  • Numbers can be….. exciting?!?

    CJ has to be the most in tune CFO out there.

    (5 Star for Nancy)

    Apple Podcasts
    5
    MitchFromBradley
    United States2 years ago
  • Run, don’t walk… to listen to this podcast!

    If you’ve ever plugged into CJ’s content on Substack, you know what to expect: high quality coverage of a variety of financial topics in an easy to consume package. Run the Numbers picks up in audio form where the newsletter leaves off, with high quality guests and really engaging conversations. (Who knew that a deep dive into TAM could be such a fun listen?) If you’re a CFO or SaaS pro looking to level up, I’d highly recommend tuning in!

    Apple Podcasts
    5
    ArlieLP
    United States2 years ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

The host delivers high-quality conversations with depth on financial topics.
Guests provide practical CFO-level insights that are easy to apply.
The show is seen as a must-listen for SaaS and fintech finance teams.
Listeners praise the mix of startup finance and AI-enabled accounting discussions.

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Talking Points

Recent interactions between the hosts and their guests.

E67: Navigating the Era of "AI Slop" in Accounting with Luke Frye
Q: If a firm wants to start adopting AI, where should they begin?
Begin with a clear vision and 90-day plan, invest in sales and CRM while aligning operations to support growth, and start on core processes like reconciliations and data onboarding—then gradually expand as they build capabilities.
E64: Numeral CEO Sam Ross: Why I Abandoned My Profitable Business to Raise $50M for Something "Boring"
Q: What do you think was the thing that got them really excited about Numeral?
We're in a complex e-commerce space that has more traction and potential return, combined with a strong product focus from our engineering team.
E64: Numeral CEO Sam Ross: Why I Abandoned My Profitable Business to Raise $50M for Something "Boring"
Q: What is the most boring AI mean to you?
It means addressing the complexities of sales tax compliance, which many find tedious rather than flashy.
E62: From Divvy FP&A to Parallel Founder: How Renato Villanueva Built the Tool Finance Actually Wants
Q: What are you most proud of in the last three months especially?
Renato is proud of learning to build a trusting team and delegating effectively, which has enhanced the team's performance and bonding.
E62: From Divvy FP&A to Parallel Founder: How Renato Villanueva Built the Tool Finance Actually Wants
Q: What was the biggest challenge so far or the biggest surprise in the fundraising process?
Renato wished he had known the importance of nurturing relationships with investors, as this significantly impacts fundraising success.

Audience Metrics

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Frequently Asked Questions About This Podcast

What is This Podcast about and what kind of topics does it cover?

Finance-focused conversations with a CFO lens, heavy on B2B fintech, AI-driven accounting and automation, and how startups scale financial operations. Episodes consistently explore funding, regulatory challenges, and innovative tools reshaping treasury, tax, and bookkeeping for high-growth companies. Notable is a strong emphasis on practical finance leadership insights, real-world implementation of AI in finance, and a track record of high-profile guest founders and operators shaping the space.

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How many episodes of this podcast are there?

this podcast launched 3 years ago and published 67 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on this podcast?

Recent guests on this podcast include:

1. Luke Frye
2. Greg Capitolo
3. Tarek Alaruri
4. Sam Ross
5. Usman Gul
6. Renato Villanueva
7. Yogi Goel
8. Dan Westgarth

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