In this episode, Sasha Orloff speaks with Usman Gul, founder and CEO of Metal, about building an AI-driven operating system for fundraising backed by Y Combinator and Andreessen Horowitz that helps founders avoid wasting 80% of their investor meetings by using data-driven insights to identify the most likely investors based on historical funding patterns, industry benchmarks, and relationship intelligence across over 500,000 venture rounds.

--

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/gulsf/

http://www.metal.so

--

X/SOCIAL:

@usmangul (Usman)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:44) Intro

(01:28) Meet Usman Gul from Metal

(01:59) Genesis of Metal

(04:32) Metal's AI-driven fundraising solutions

(08:08) Common fundraising mistakes and solutions

(13:24) Sponsors: Notion | Puzzle

(14:15) Importance of modern tools for startups

(21:40) Metal manifesto

(24:35) Key indicators for successful fundraising

(25:53) Telling the right story to investors

(26:44) Challenges and insights from previous ventures

(27:13) Evolution of investor targeting

(28:38) Predictive intelligence and the future of Metal

(30:41) Current state of fundraising tools

(36:53) Building Metal with minimal capital

(39:19) Advice for founders on fundraising

(47:29) Wrap

In this episode, Sasha Orloff speaks with Renato Villanueva, Founder and CEO of Parallel, about his journey from finance professional at Divvy to raising $2.4 million from Bain Capital and K5 Tokyo Black for an AI-powered FP&A platform that helps founders model financial scenarios and make confident growth decisions. Renato shares lessons on building products founders are passionate about rather than forced wedges, nurturing investor relationships, and how Parallel's approach has enabled customers to achieve significant growth—including one company that scaled from planning one sales hire to four, ultimately raising one of Utah's biggest Series A rounds.

--

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/villanuevar/⁠

https://www.getparallel.com/

--

X/SOCIAL:

@_renatov (Renato)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(01:24) Intro

(02:09) Meet Renado Villanueva

(02:38) Renado's journey to founding Parallel

(04:02) Moment of decision

(04:45) Building the deck and quitting the job

(09:20) Challenges and insights in fundraising

(11:05) What Parallel actually does

(14:24) Sponsors: Notion | Puzzle

(15:49) Parallel’s target sweet spot

(16:49) Common mistakes founders make

(19:30) AI's role in finance decision-making

(20:15) Balancing flexibility and opinion in software

(23:11) Who should use Parallel?

(25:06) Excel vs. Parallel: Finding the right balance

(27:06) Evolution of FP&A tools

(31:24) Lessons learned from building Parallel

(35:34) Building and trusting a team

(38:31) Future of Parallel

(39:47) Wrap

In this episode, Sasha Orloff talks with Yogi Goel, Co-founder and CEO of Maxima, about raising $41 million from Kleiner Perkins and RedPoint Ventures to build an agentic AI platform for enterprise accounting that automates journal entries, reconciliations, and variance analysis for complex companies, helping them close their books 2-3 days faster with 98% automation while strengthening SOX controls and freeing accountants from mundane tasks.

--

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/yogi-goel/

https://www.maxima.ai/

--

X/SOCIAL:

@maxima_dot_ai (Maxima)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:50) Intro

(01:34) Introducing Yogi Goel and Maxima

(02:08) Problem with traditional accounting

(04:50) Birth of Maxima

(07:03) Maxima's solutions and innovations

(11:19) Sponsors: Notion | Puzzle

(12:43) Customer success stories

(25:08) Future of accounting with AI

(27:10) Fundraising and growth

(29:53) Advice for founders and CFOs

(34:15) Embracing AI: Overcoming fear and finding solutions

(35:56) Getting in touch with Maxima

(36:17) Story behind the name 'Maxima'

(37:01) Wrap

In this episode, Sasha Orloff sits down with Dan Westgarth, COO of Deel, to explore how the company scaled to 37,000 customers, processes $22B in payroll, and recently raised a $300M Series E to power global hiring in 150 countries. They dive into the future of back-office automation, including real-time payroll, AI-driven operations, and the push toward a unified, seamless global HR and accounting stack.

--

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/dan-westgarth-710650a4/

https://www.deel.com/

--

X/SOCIAL:

@DanWestgarth (Dan)

@deel (Deel)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:44) Introduction to Tech Finance

(01:25) Meet Dan Westgarth, COO of Deel

(02:18) Dan's journey with Revolut

(06:22) Building Deel's global infrastructure

(08:33) Managing global operations

(12:06) Expanding Deel's services

(19:56) Importance of consolidation

(21:15) Sponsors: Notion | Puzzle

(22:55) Common mistakes startups make

(24:09) Onboarding and implementation challenges

(25:46) Customer engagement and feedback

(28:23) Recruiting and hiring strategies

(31:27) Future of accounting and payroll

(40:53) Real-time payroll processing

(44:09) Wrap

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.

--

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://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.

--

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.

--

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