In this episode, CJ is joined by Lee Kirkpatrick, the former CFO of the cloud communications platform, Twilio. Lee shares his journey of leading Twilio through its 2016 IPO, shedding light on the preparations, roadshows, and decisions (bankers, soundtrack, tv appearances) made at different stages of the process. This is inside baseball to taking your company public - a must listen.  If you’re looking for an ERP platform, check out our sponsor, NetSuite: https://netsuite.com/metrics
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SPONSORS:
NetSuite provides financial software for all your business needs. More than 37,000 thousand companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅ NetSuite: https://netsuite.com/metrics and get a customised KPI checklist.

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

Thoropass provides complete compliance management, continuous monitoring, and security audits through intuitive software and expert guidance – allowing you to do business with confidence. Learn more: https://bit.ly/Thoropass 🔒

Tropic is the next-generation Procurement Platform that’s helping modern CFOs take control of their budgets and bottom line. By combining approval workflows, supplier management, and pricing benchmarks all in one place, Tropic makes savings opportunities easy to find and act on. 🌴 Visit www.tropicapp.io/metrics to learn how.
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LINKS:
RingCentral's CFO on Public Earnings Calls: https://www.youtube.com/watch?v=FUxRD89qTJc
--
FOLLOW US ON X:
@cjgustafson222 (CJ)
@turpentinemedia
--
TIMESTAMPS:
(00:00) Intro + Sponsors: NetSuite | Thoropass
(05:20) Lee's Preparation for Going Public
(07:05) Twilio had No Comps
(12:39) Twilio's IPO Day Experience
(18:29) Sponsors: Maxio | Tropic
(20:46) IPO Pricing Strategy
(24:44) Choosing the Right Bankers for an IPO
(27:00) Selecting Investors for a Successful IPO
(28:34) The Reality of Investor Promises
(29:53) The Grueling Roadshow Experience
(34:56) Preparing for the First Earnings Call as a Public CFO
(39:38) The Art of Disclosing and Guiding Metrics
(41:10) The Qualities of a Great CFO
(42:29) Learning from Mistakes and Ego in Leadership
(45:58) The Craziest Expense Report Story

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Today CJ hosts Dave Yuan, the founder and partner at Tidemark — a legend in the world of vertical SaaS. Dave has been investing, advising, and building technology companies for over 20 years. Before founding Tidemark, Dave spent 15 years as a general partner at Technology Crossover Ventures (TCV), where he was fortunate to invest in and help 25 companies scale and win. Twelve companies have gone public, and eight have been acquired. Today’s conversation covers key heuristics, what’s wrong with classical vertical SaaS strategies, and the importance of thinking multi-product early on. This is a master class in how vertical SaaS companies come to dominate a market and a deep dive into the metrics they stay close to along the way.

As mentioned during the episode, Tidemark is launching its first annual Vertical and SMB SaaS Benchmark survey. You can complete the survey here if you’re a vertical SaaS or SMB/horizontal leader (https://www.surveymonkey.com/r/DXPNVWM). It is completely anonymous and takes ~10 minutes to complete. If you’re interested, the Tidemark team can walk you through your results compared to your peers. Survey participation also helps provide valuable insights in support of the broader vertical SaaS ecosystem and benefits your fellow operators.
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SPONSORS: Maxio | Tropic | Thoropass

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

Tropic is the next-generation Procurement Platform that’s helping modern CFOs take control of their budgets and bottom line. By combining approval workflows, supplier management, and pricing benchmarks all in one place, Tropic makes savings opportunities easy to find and act on. 🌴 Visit www.tropicapp.io/metrics to learn how.

Thoropass provides complete compliance management, continuous monitoring, and security audits through intuitive software and expert guidance – allowing you to do business with confidence. Learn more: https://bit.ly/Thoropass 🔒
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LINKS:
Tidemark's 2024 SMB and Vertical SaaS Benchmarks Survey: https://www.surveymonkey.com/r/DXPNVWM
If you liked this episode, check out Alex Clayton of Meritech on Run the Numbers: https://podcasts.apple.com/us/podcast/a-saas-metrics-deep-dive-with-alex-clayton/id1704418764?i=1000638155836
---
FOLLOW US ON X:
@cjgustafson222 (CJ)
@davelyuan (Dave)
@tidemark_vskp (Tidemark)
---
TIMESTAMPS:
(00:00) Intro + Sponsors: Maxio | Tropic
(04:26) Understanding Vertical SaaS
(07:16) Dave’s Investing Strategy
(09:55) Understanding Control Points in Vertical SaaS
(12:40) Sponsor: Thoropass
(19:24) The Journey to Multi-Product
(22:35) Debunking the Layer Cake Model in Vertical SaaS
(27:19) Exploring Multiplayer vs Marketplace in Vertical SaaS
(28:53) Marketplaces
(32:11) Challenges Faced by Marketplaces
(34:00) Vertical SaaS Companies: Obstacles and Opportunities
(36:01) Vertical Integration
(40:16) Key Metrics 
(48:58) Fair Harbor case study: A Vertical SaaS Success

Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

Tony Kim, Managing Director at Blackrock, joins CJ this week to touch on the secrets of durable businesses, why TAM is an unreliable measure of potential, competitive moats and 2nd/3rd acts as necessary means for sustainable growth, and more. Supercharge your financial operations with Maxio. Request a demo at www.maxio.com/runthenumbers for 10% off your first year.
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SPONSORS: Maxio | Tropic | Thoropass

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

Tropic is the next-generation Procurement Platform that’s helping modern CFOs take control of their budgets and bottom line. By combining approval workflows, supplier management, and pricing benchmarks all in one place, Tropic makes savings opportunities easy to find and act on. 🌴 Visit www.tropicapp.io/metrics to learn how.

Thoropass provides complete compliance management, continuous monitoring, and security audits through intuitive software and expert guidance – allowing you to do business with confidence. Learn more: https://bit.ly/Thoropass 🔒
---
FOLLOW US ON X:
@cjgustafson222 (CJ)
@TurpentineMedia (Turpentine)
---
TIMESTAMPS:
00:00:00: Introduction
00:03:03: Definition and importance of durable revenue
00:05:35: Evaluating net dollar retention rate
00:09:08: Importance and calculation of TAM
00:16:45: Deconstructing and understanding real TAM
00:18:51: Thin wrappers and positioning companies
00:25:00: Comparing tech quality over different eras
00:28:58: Maturity and market attention for public companies
00:31:58: Necessity of moats and dominance in business
00:36:06: Evaluating companies
00:36:42: The importance of the second act in business
00:41:11: The value of a strategic narrative
00:45:02: What separates good CFOs from great CFOs

Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

Jonathan Becker, CEO of Thrive Digital, breaks down learnings from his 12+ years of running data-led marketing campaigns for top startups like Uber, Asana, and Square. Supercharge your financial operations with Maxio. Request a demo at www.maxio.com/runthenumbers for 10% off your first year.
---
SPONSORS: Maxio | Tropic | Thoropass

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

Tropic is the next-generation Procurement Platform that’s helping modern CFOs take control of their budgets and bottom line. By combining approval workflows, supplier management, and pricing benchmarks all in one place, Tropic makes savings opportunities easy to find and act on. 🌴 Visit www.tropicapp.io/metrics to learn how.

Thoropass provides complete compliance management, continuous monitoring, and security audits through intuitive software and expert guidance – allowing you to do business with confidence. Learn more: https://bit.ly/Thoropass 🔒
---
FOLLOW US ON X:
@cjgustafson222 (CJ)
@TurpentineMedia (Turpentine)
---
TIMESTAMPS:
00:00:00: Introduction
00:05:07: Google as a money-making machine
00:07:20: Differences between brand marketing and performance marketing
00:11:00: On scaling and reach of marketing
00:18:13: The Importance of understanding Customer Acquisition Cost (CAC) and Lifetime Value (LTV)
00:20:03: Metrics in marketing
00:23:43: Marketing Efficiency ratio explanation
00:30:46: Hiring and building a marketing team
00:37:14: Psychology of impatience in advertising
00:42:13: Setting clear expectations in marketing tests
00:45:23: Good campaign attribution
00:52:25: Expedia's digital marketing success story
00:54:07: Athletic Greens' success story
00:56:00: Grammarly's adoption on YouTube
00:57:36: Costs and impact of Super Bowl ads

Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

Sebastian Duesterhoeft, partner at Lightspeed Ventures, returns to the pod to talk about anything and everything startup operators need to know about Competitive Moats aka the durable competitive advantage of a company. Supercharge financial operations with Maxio. Request a demo at www.maxio.com/runthenumbers for 10% off your first year.
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SPONSORS: Maxio | Tropic | Thoropass

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

Tropic is the next-generation Procurement Platform that’s helping modern CFOs take control of their budgets and bottom line. By combining approval workflows, supplier management, and pricing benchmarks all in one place, Tropic makes savings opportunities easy to find and act on. 🌴 Visit www.tropicapp.io/metrics to learn how.

Thoropass provides complete compliance management, continuous monitoring, and security audits through intuitive software and expert guidance – allowing you to do business with confidence. Learn more: https://bit.ly/Thoropass 🔒
---
FOLLOW US ON X:
@cjgustafson222 (CJ)
@lightspeedvp (Lightspeed)
@TurpentineMedia (Turpentine)
---

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In this episode, Hubspot SVP of RevOps Sid Kumar discusses the most crucial aspects of revenue operations, the importance of data strategy, perspectives on rep productivity and commission structures, discounting, and more. The conversation also touches on how the lines between go-to-market and product strategies are increasingly blurring. Sid also gives us his take on comp plan design. Supercharge financial operations with Maxio. Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

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SPONSORS: Maxio | Tropic | Thoropass

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

Tropic is the next-generation Procurement Platform that’s helping modern CFOs take control of their budgets and bottom line. By combining approval workflows, supplier management, and pricing benchmarks all in one place, Tropic makes savings opportunities easy to find and act on. 🌴 Visit www.tropicapp.io/metrics to learn how.

Thoropass provides complete compliance management, continuous monitoring, and security audits through intuitive software and expert guidance – allowing you to do business with confidence. Learn more: https://bit.ly/Thoropass 🔒

---
FOLLOW US ON X:
@cjgustafson222 (CJ)
@sidkumar (Sid)
@TurpentineMedia (Turpentine)
---
TIMESTAMPS:
(00:00) Intro
(00:36) Where does RevOps sit?
(03:38) The Intersection of RevOps and Finance
(04:43) When to Hire the First RevOps Person
(05:45) The Role of Data in RevOps
(08:27) The Relationship Between FP&A and RevOps
(10:33) Designing Effective Commission Plans
(12:39) The Role of Incentives and Outcomes in RevOps
(18:57) Sponsors: Maxio | Tropic
(22:22) The Importance of Agile Planning in RevOps
(26:01) Understanding Sales Capacity and Quota Assignment
(27:15) AI and Product Led Growth: Blurring the Lines
(27:43) Understanding Business Segmentation
(32:20) Sponsor: Thoropass
(33:40) The Philosophy of Discounting
(37:32) The Role of Spiffs in Sales
(41:09) Understanding Rep Productivity Metrics
(48:29) The Role of Communication in CFO Success
(50:41) The Impact of Large Commission Checks

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CJ welcomes the president of the Boston Celtics, Rich Gotham. Rich discusses his journey in the NBA and provides insight into the business side of one of the world's most recognizable sports brands. He highlights the emphasis placed on embracing digital technology, retaining fans, creating effective partnerships, and the importance of community involvement for the team. Rich also talks about the increasing role of data in managing team operations and addresses the famous Paul Pierce incident from the 2008 NBA Finals. Supercharge financial operations with Maxio. Request a demo at www.maxio.com/runthenumbers for 10% off your first year.
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SPONSORS: Maxio | Tropic | Thoropass

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

Tropic is the next-generation Procurement Platform that’s helping modern CFOs take control of their budgets and bottom line. By combining approval workflows, supplier management, and pricing benchmarks all in one place, Tropic makes savings opportunities easy to find and act on. 🌴 Visit www.tropicapp.io/metrics to learn how.

Thoropass provides complete compliance management, continuous monitoring, and security audits through intuitive software and expert guidance – allowing you to do business with confidence. Learn more: https://bit.ly/Thoropass 🔒
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TIMESTAMPS:
(00:00) Intro
(00:44) The Evolution of the Boston Celtics' Business Model
(00:49) The Impact of Digital Technology on the Celtics' Business
(02:33) The Challenges of a Finite Business Model
(08:41) The Impact of Team Performance on Revenue
(10:54) The Role of Sponsorship in the Celtics' Business
(13:47) Sponsor: Maxio | Tropic
(16:09) Playoffs and Revenue Generation
(23:28) The Role of Data in the Celtics' Business
(26:30) Enhancing the Fan Experience
(28:01) The Importance of Retention Rate
(28:11) Renewal Planning and Timing
(29:24) Sponsor: Thoropass
(30:40) Estimating the Lifetime Value of a Fan
(30:55) The Importance of Community Engagement
(32:13) The Impact of High Renewal and Retention Rate
(32:31) Revenue Generation from Different SKUs
(33:08) The Importance of Branding and Merchandising
(34:05) Learning from Other Sports Organizations
(36:26) The Unique Culture of Sports Industry
(36:54) The Competition for Fans' Time
(38:21) Long Ass Lightning Round: Career Advice and Insights

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In this episode, Bonfire VC partner Brett Queener, who was also the first sales ops and sales strategy person at Salesforce, shares insights on staffing ratios and building sales capacity. Brett unleashes his wisdom on driving alignment and setting sales quotas, forecasting revenue for new products, targeting existing customers vs. net new, the importance of sales enablement, expanding product offerings and TAM, the risks of predicting revenue for new products, long-term forecasting and investment, and avoiding an identity crisis. Supercharge financial operations with Maxio. Request a demo at www.maxio.com/runthenumbers for 10% off your first year.
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SPONSORS: Maxio | Tropic | Thoropass

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

Tropic is the next-generation Procurement Platform that’s helping modern CFOs take control of their budgets and bottom line. By combining approval workflows, supplier management, and pricing benchmarks all in one place, Tropic makes savings opportunities easy to find and act on. 🌴 Visit www.tropicapp.io/metrics to learn how.

Thoropass provides complete compliance management, continuous monitoring, and security audits through intuitive software and expert guidance – allowing you to do business with confidence. Learn more: www.thoropass.com.
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LINKS:
Brett's resources and templates for founders, strategy, and CFOs: https://www.bonfirevc.com/fuel
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FOLLOW US ON X:
@cjgustafson222 (CJ)
@bqueener (Brett)
@TurpentineMedia (Turpentine)
---
TIMESTAMPS:
00:00 Introduction and Guest Welcome
00:19 Sales Strategy and Capacity Planning at Salesforce
00:39 The Evolution of On-Premise Companies
01:28 The Shift to Salesforce and the SAS Model
02:34 Building Your Own Army: Salesforce's Growth Strategy
02:50 Staffing Ratios and Sales Capacity
03:57 The Importance of Efficient Spending in Business
04:27 The Role of High Quality Developers and Account Executives
05:04 The Impact of Overfunding and Changing Goalposts
05:09 Understanding Business Economics and Balancing Growth
05:48 The Importance of Staffing Ratios in Sales Organizations
07:07 The Role of Salespeople in Business Growth
08:06 Understanding Business Segments and Hiring Perspectives
08:42 The Role of Marketing in Different Business Segments
09:32 The Importance of Understanding Your Business and Its Segments
11:47 The Role of Sales Capacity in Business Growth
13:55 The Importance of Forecasting in Business
15:28 The Role of Sales Rep Compensation in Business
18:52 Sponsor: Maxio | Tropic
20:12 The Role of Procurement in Business
21:15 Understanding the Ratio of Quota to OTE
25:21 The Importance of Growing Your Reps to Outrun Your Expenses
27:09 Understanding the Impact of Attrition in Business
30:19 Sponsor Break: Thoropass
30:52 Introducing a New Way of Doing InfoSec Audits
31:41 Exploring the Technical Side of the Business
32:26 Understanding the Importance of Developers and Salespeople
34:45 The Role of Product Management in a Tech Company
37:38 The Importance of a Strong Product Leader
41:41 The Challenges of Launching New Products
49:16 The Importance of Long-Term Forecasting
55:41 Understanding the Identity and Potential of Your Company
57:42 Closing Remarks and Contact Information

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Matthew Newcomb, the CFO of Chime, joins host CJ Gustafson to delve into the complex world of the payments ecosystem. Matthew demystifies the business model of neobanks, different types of transactions, as well as how unit economics plays a key role in a neobank's business model and strategy. CJ's intro is about the controversy at Carta. Supercharge financial operations with Maxio. Request a demo at www.maxio.com/runthenumbers for 10% off your first year.
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SPONSORS: Maxio | Tropic

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

Tropic is the next-generation Procurement Platform that’s helping modern CFOs take control of their budgets and bottom line. By combining approval workflows, supplier management, and pricing benchmarks all in one place, Tropic makes savings opportunities easy to find and act on. 🌴 Visit www.tropicapp.io/metrics to learn how.
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X / TWITTER:
@matthewsnewcomb (Matthew)
@cjgustafson222 (CJ)
@TurpentineMedia (Turpentine)
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TIMESTAMPS:
(00:00) Intro
(00:40) What happened at Carta?
(12:59) Matt talks about the ways that FinTech companies monetize their business models
(15:40) Making money off of free products
(17:50) Chime and the bank partnership model
(22:10) On user or engagement activity and acquiring banking relations
(23:26) Sponsor: Maxio
(24:50) Innovating to get things to go faster without breaking the rules and stepping on some toes
(27:20) How have the competitive moats either for Chime or in the industry evolved over time?
(33:00) Does fundraising for companies like Chime any different than fundraising for a typical SaaS company?
(35:00) The differences in costs between an ACH, a wire and an instant transfer
(37:35) B2C neobanks and B2B neobanks - are there any key distinctions between the two besides the customer?
(38:24) The lifetime value of a Chime user
(42:44) Chime's North star metric
(45:00) On the qualities that separate a good CFOs from a great CFO
(49:40) Matt's example of something he's screwed up on the job
(51:00) What would Matt tell his younger self knowing what he knows today?
(52:10) Rep Yo Stack sponsored by Tropic 🌴

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Your most pressing questions are answered today by CJ Gustafson and Kurtis Hanni. They tackle Q's such as how best to scale the finance department for startups, what keeps them up at night, and predictions for how the CFO role will change in the near future. They also offer advice about cold emailing, relating to money, and dunking. Kurtis Hanni is a SMB CFO and writer of Frameworks & Finance (https://www.kurtishanni.com/blog)

🎧 Run The Numbers has a new Spotify and Apple show link. Follow the links to subscribe and ensure you'll never miss an episode. Give us 5 stars while you're at it!
Apple: https://podcasts.apple.com/us/podcast/run-the-numbers/id1723787140
Spotify: https://open.spotify.com/show/0zQCkklNnVgMD364kCW5SV
---
SPONSORS: Maxio | Tropic

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.Maxio.com/runthenumbers for 10% off your first year.

Tropic is the next-generation Procurement Platform that’s helping modern CFOs take control of their budgets and bottom line. By combining approval workflows, supplier management, and pricing benchmarks all in one place, Tropic makes savings opportunities easy to find and act on. 🌴 Visit www.tropicapp.io/metrics to learn how.
---
X / TWITTER:
@kurtishanni (Kurtis)
@cjgustafson222 (CJ)
@TurpentineMedia (Turpentine)
---
TIMESTAMPS:
(00:00) Intro
(00:41) Stupidest CFO moves
(02:40) Most common pain points that are keeping CEOs up at night?
(11:01) Sponsor - Maxio
(12:10) What does scaling the finance department look like for startup companies?
(18:39) Sponsor - Tropic
(30:37) What's the number one thing you attribute your career success to?
(41:30) What, if anything, do you think will change about the CFO role five to 10 years from now?
(47:00) Do you have any tactics for getting important people to answer cold emails?

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