In this episode, Sasha Orloff talks with Nick Abouzeid, Co-founder and CEO of Rivet, about raising venture capital from XYZ, Haystack, and other angels to build a modern tax and accounting firm that serves 600+ category-defining companies like Cursor by combining world-class tax practitioners with custom-built software infrastructure, delivering premium responsive service while challenging the traditional accounting firm model of unresponsive service and outdated technology.

--

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.rivet.tax

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

--

X/SOCIAL:

@nickabouzeid (Nick)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:36) Intro

(01:21) Meet Nick Abouzeid, CEO of Rivet

(01:57) Rivet unique approach to tax services

(02:52) Challenges in the tax preparation market

(06:59) Human element in AI-powered tax services

(09:33) Journey to venture capital

(14:29) Sponsors: Notion | Puzzle

(15:54) Scaling and surprises in building Rivet

(18:23) Open roles and team dynamics

(19:00) Feedback and roadmap development

(19:24) International hiring and cost efficiency

(20:40) Data integration challenges

(21:23) Future of AI in accounting

(22:58) Complexity in tax code and software

(23:30) Human expertise vs. AI

(32:23) Pricing models in tax preparation

(34:26) Client success stories

(36:29) Looking forward: New hires and future plans

(37:16) Wrap

In this episode, Sasha Orloff sits down with Blake Hutchison, CEO of Flippa, to discuss the launch of Lauren AI—Flippa’s new AI tool transforming how online businesses are bought and sold. They explore how Lauren AI uses proprietary data and machine learning to enhance deal sourcing, automate buyer outreach, and streamline deal structuring. The conversation also dives into how AI is reshaping small business M&A, making exits and acquisitions more accessible, efficient, and competitive for entrepreneurs worldwide.

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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/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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RECOMMENDED IN THIS EPISODE:

https://flippa.com/product/dealsourcing/

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

--

X/SOCIAL:

@Flippa (Flippa)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:32) Intro

(01:01) Interview with Blake Hutchison, CEO of Flippa

(01:45) Introducing Lauren AI

(02:15) How Lauren AI Enhances deal sourcing

(07:05) Real-life example of Lauren AI in action

(13:08) Sponsors: Notion | Puzzle

(14:35) Matching engine and AI capabilities

(17:38) Buyer experience and mandate creation

(19:21) Lauren AI: Enhancing buyer profiles

(21:33) Outreach and CRM integration

(23:59) AI's role in M&A processes

(28:33) Leveling the playing field for small buyers

(31:11) Fair pricing and exit readiness

(37:04) Wrap

In this episode, Sasha Orloff sits down with Jason Mok, VP & GM of Startups at Brex, about the company's evolution from credit cards to a comprehensive financial platform and their new partnership with Puzzle to offer "one-click accounting" that automatically sets up bookkeeping for startups during Brex onboarding, eliminating the friction that typically delays founders from getting proper financial infrastructure in place from day one.

--

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/jasonmok/

https://www.brex.com/

--

X/SOCIAL:

@jasonmok (Jason)

@brexHQ (Brex)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:50) Intro

(01:18) Live from Brex offices with Jason Mock

(02:19) Early days of Brex and startup credit challenges

(04:20) Silicon Valley bank's role in the startup ecosystem

(12:26) From SVB to Andreessen Horowitz

(18:50) Sponsors: Notion | Puzzle

(20:13) Bridging the knowledge gap for first-time founders

(22:48) Joining Brex during a time of change

(28:02) Starting at Brex: Initial goals and challenges

(28:52) Evolving role and team growth

(29:39) Bespoke go-to-market strategies

(32:08) Defining startups at Brex

(36:54) Importance of accounting for startups

(42:25) Introducing one-click accounting

(46:52) Partnerships and future vision

(55:13) Wrap

In this episode, Sasha Orloff talks with Joe Faris, founder of Accountalent, about his four decades of helping over 5,000 startups navigate tax and accounting challenges, covering critical founder lessons from 83B elections and R&D tax credits to payroll compliance and bookkeeping best practices that can save startups from costly mistakes and penalties.

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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/farisjoe/

https://accountalent.com/

--

X/SOCIAL:

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:55) Intro

(01:24) Meet Joe Ferris: Startup tax expert

(03:24) Joe's journey: From Shell oil to startups

(06:46) Birth of Accountalent

(09:14) Navigating the financial crisis

(13:32) Adventures in IPOs and legal battles

(19:33) Sponsors: Notion | Puzzle

(21:18) Lessons for founders: Payroll pitfalls

(23:21) Introduction to payroll medic

(23:39) Understanding tax compliance for startups

(26:37) Importance of bookkeeping

(27:55) Unbook keeper for founders

(29:08) Setting up and managing bookkeeping systems

(35:44) Role of RD tax credits

(38:32) Lessons learned from working with startups

(39:51) Impact of good accounting and tax strategy

(42:29) Wrap

In this episode, Sasha Orloff talks with Josh Wymer, Co-founder and CEO of Central HQ, about raising $8.6 million from First Round Capital and Y Combinator to build an AI-first back office solution that eliminates business compliance tasks through Slack-based automation, helping startups handle payroll, taxes, and HR without the administrative burden that typically comes with traditional software.

--

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/joshwymer/

https://centralhq.com/

--

X/SOCIAL:

@jbwyme (Josh)

@CentralHQX (Central HQ)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(01:03) Intro

(01:46) The unavoidable hassles

(02:20) Meet Josh Wymer: The mission to eliminate business BS

(02:57) Complexity of payroll and compliance

(04:48) Central’s vision: Simplifying the back office

(07:19) Challenges and innovations in payroll solutions

(10:10) Sponsors: Notion | Puzzle

(11:35) Future of AI in business operations

(18:42) Power of LLMs and AI in streamlining tasks

(21:42) Origin of the tagline

(23:41) Investor reactions and brand strategy

(24:36) Challenges in a competitive market

(25:32) Focusing on founders and SMBs

(28:51) Learning and iterating as a startup

(33:21) Misunderstandings and common mistakes

(36:44) Future of startups and SMBs

(38:42) Wrap

In this episode, Sasha Orloff talks with Ben Taylor, CEO & Co-founder of SoftLedger, about bootstrapping a modern, API-first general ledger that helps finance teams manage multi-entity businesses beyond QuickBooks without the complexity of Netsuite.

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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/bentaylor8/

⁠https://softledger.com

--

X/SOCIAL:

@SoftLedger (SoftLedger)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:40) Intro

(01:09) Meet Ben Taylor, CEO & Co-founder of SoftLedger

(02:36) Origin story of SoftLedger

(03:11) Target market and unique selling points

(07:14) Evolution of the accounting software market

(08:21) AI in accounting: Opportunities and challenges

(11:08) Sponsors: Notion | Puzzle

(12:31) SoftLedger's approach to AI integration

(17:34) Choosing the right accounting software for complex enterprises

(19:16) Customer success stories: Eco G energy

(22:31) Challenges and surprises in building accounting software

(26:58) Importance of multi-entity consolidation

(31:53) Fundraising journey and efficient growth

(34:16) Future plans and market expansion

(37:03) Wrap

In this episode, Sasha Orloff and Alex Lee, Co-founder & CEO of Truewind, to discuss how his company is transforming accounting with AI-powered automation—streamlining tasks like data reconciliation and deposit matching from hours to minutes. They explore Truewind’s journey, recent funding led by Thomson Reuters and Row Capital, and the future of accounting through AI, autonomous agents, and customer-centric innovation.

--

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/alexlee611/

https://www.truewind.ai/

--

X/SOCIAL:

@AlexLee611 (Alex)

@truewindai (Truewind)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:28) Intro

(01:07) Guest Introduction: Alex Lee from Truewind

(02:27) Origin of Truewind

(06:18) Impact of AI on accounting

(08:24) Adoption of AI in accounting

(09:59) Future of finance and accounting teams

(12:09) Truewind's approach and strategy

(15:13) Role of automation in accounting

(17:12) Sponsors: Notion | Puzzle

(18:49) Digital staff accountant concept

(19:53) Exploring AI features in finance

(21:07) Government regulations and data sharing

(22:23) Exciting news: Fundraising success

(24:08) Customer-centric approach to product development

(24:57) Advice for founders on fundraising

(27:15) Defining success for Truewind

(35:55) Future of finance and AI integration

(37:08) Wrap

This week, Sasha Orloff sits down with Will Hubbard, Founder & COO of Agree, about building an all-in-one platform that streamlines contracting, invoicing, billing, and payments. They explore Agree’s rapid growth, recent $7.2M seed round, and how AI and user-centered design are shaping the future of finance tech.

--

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/wbhub/

https://agree.com/

--

X/SOCIAL:

@wbhub (Will)

@AgreeHQ (Agree)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:41) Intro

(01:23) Meet Will Hubbard: The story behind Agree

(02:19) Agree: All-in-one contracting and invoicing platform

(02:54) Evolution of Agree: From venture fund to B2B payments

(03:54) Delightful user experience of Agree

(06:06) Importance of design in accounting software

(06:57) The Why Now: Bundling contracting and invoicing

(08:51) Innovative features and AI-driven development

(13:38) Sponsors: Notion | Puzzle

(15:03) Favorite features: Tracking and reminders

(17:34) Surprising use cases and rapid development

(20:03) Viral growth of Agree.com

(21:22) Story behind Agree.com

(23:25) Challenges in naming a company

(24:57) Raising the next round of funding

(27:26) Future plans and product development

(29:11) Advice for finance leaders and founders

(34:22) Future of finance: Humans plus software

(35:37) Wrap

In this episode, Sasha Orloff talks with Ali Hussain, CEO of Tabs, discuss how the company is using AI to modernize revenue and collections management, reduce DSO, and boost efficiency for finance teams. They discuss Ali’s journey from PhD dropout to fintech founder, Tabs’ $25M raise, and how the platform is reshaping B2B finance operations.

--

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/ali-hussain786

https://tabs.inc/

--

X/SOCIAL:

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(01:04) Intro

(01:43) Meet Ali Hussain

(03:20) Vision behind Tabs

(07:41) Challenges and opportunities in finance automation

(11:06) Future of finance teams

(15:29) Sponsors: Notion | Puzzle

(16:53) Case study: Success with Statik

(19:09) Example of Tabs in action

(19:49) Future of AI in finance

(21:41) Agentic future and trust

(23:52) Building operational software

(27:32) Favorite features and lessons learned

(30:32) Venture capital and market opportunity

(34:05) Advice for founders

(36:58) Future plans and excitement

(41:41) Wrap

This week, Sasha Orloff and Zuora CFO Todd McElhatton discuss the growing complexity of finance operations and the critical role of AI in modern accounting. They talk about the insights from the 'Modern Finance Leader' report, strategies for overcoming legacy systems, and practical advice for finance leaders navigating technological change.

--

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/todd-mcelhatton-2140761/

https://www.zuora.com/resource/modern-finance-leader-report/_

--

X/SOCIAL:

@Zuora (Zuora)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:43) Intro

(01:11) Season 2 focus: Accounting and technology

(01:30) Insights from the Modern Finance Leader Report

(02:13) Interview with Todd McElhatton: Challenges in finance technology

(05:34) The modernization Catch 22

(09:08) AI and the future of finance

(13:46) Sponsors: Notion | Puzzle

(15:26) Practical advice for finance leaders

(16:53) Zuora's impact and client success

(19:20) Role of AI and automation

(21:13) Building a 'Yes' department

(23:27) Advice for new finance leaders

(25:46) Transforming existing finance teams

(30:14) Strategic investment in technology

(32:22) Evolving role of CFOs

(34:21) Joining Zuora and making an impact

(35:29) Client success and product value

(36:39) Wrap