Run the Numbers CJ Gustafson

Silicon Valley veteran and early employee at Google, Facebook, and Quip, Molly Graham, joins CJ to discuss all things related to scaling startups, growing as a leader, and progressing in your career. Molly talks about her famous “Give Away Your Legos” talk and how this came about before she and CJ discuss the concept of “work grief” and how to get through it when you have to give up something that your identity is tied to. Having had a very non-linear career path and “stumbling sideways into things”, Molly explains the J-Curve versus staircase analogy for career progression and encourages especially those in finance roles to take big risks. From handling the grief of laying someone off to learning the skill of saying no, mastering the art of destruction as an important part of building a company, and knowing how to fire people not just hire them, Molly shares profound insights from her impressive career. 
If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.
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SPONSORS:
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.
Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com.
Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC.
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 customized KPI checklist. 
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FOLLOW US ON X:
@cjgustafson222 (CJ)
@molly_g (Molly)
MOLLY’S SUBSTACK: “Lessons”
 
“‘Give Away Your Legos’ and Other Commandments for Scaling Startups” - Molly Graham:
https://review.firstround.com/give-away-your-legos-and-other-commandments-for-scaling-startups/ 
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TIMESTAMPS:
(00:00) Preview and Intro
(01:54) Sponsor - Maxio | Mercury
(04:15) What It Means to “Give Away Your Legos”
(07:59) The Concept of “Work Grief” and How to Get Through It
(12:30) Using the Worst-case Scenario as a Motivator
(15:41) Handling the Grief of Laying Someone Off
(17:28) Sponsor - Netsuite
(18:44) The J-curve Versus Staircase Analogy for Career Progression
(27:31) The Powerful Combo of Risky Paths and Network Building
(30:45) Why You Should Take a Risk if You’re in FP&A or Finance
(33:22) What It Was Like Working Directly for Chamath at Facebook
(34:19) Learning the Skill of Saying No 
(40:18) Why It’s Okay Not to Have a Career Path Mapped Out
(42:41) Destruction as an Important Part of Building a Company
(46:04) The Skill of Time Compression for Leaders
(49:23) The Importance of Knowing How to Fire People, Not Just Hire Them
(53:58) Glue Club and Who Can Benefit From It
(55:21) Finding Your Product Market Fit at Companies of Different Sizes
(59:38) Wrap


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In this episode, CJ is joined by Lanny Baker, the CFO of Eventbrite, and former CFO of Yelp, Monster.com, and ZipRealty. Lanny has been a part of some incredible business transformations or pivots at each of these companies and has some profound insights to share on the topic. First, he explains some of the differences between consumer-facing internet businesses versus SaaS or B2B. He sheds light on Eventbrite’s unique creator and consumer model, the virtuous cycle of network effects it benefits from, and how the company’s take rate is determined. Lanny also talks about the ways that internet platforms expand their TAM over time. This leads to a conversation on business transformations or pivots, the role of a CFO in them, whether to retain or replace people in such a situation, and how to handle investors. Tune in for all this and the hilarious story about a marketing stunt gone wrong.
If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.
—
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 customized 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.
Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com.
Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC.
—
FOLLOW US ON X:
@cjgustafson222 (CJ)
—
TIMESTAMPS:
(00:00) Preview and Intro
(02:25) Sponsor - NetSuite | Maxio 
(05:16) How to “Show Up for Life” in Business
(06:54) Consumer-facing Internet Businesses Versus SaaS or B2B
(11:03) First Principles in Building Your Operating Plan as a Finance Team
(13:13) The Benefits of Eventbrite’s Unique Creator and a Consumer Model
(17:28) The Most Important Metric for Eventbrite
(19:04) Sponsor - Mercury 
(21:34) The Factors That Determine Eventbrite’s Take Rate
(25:57) How Internet Companies Expand Their TAMs Over Time
(29:46) The Role of a CFO in a Business Transformation
(40:38) Replacing Versus Retaining People in a Business Transformation
(48:08) Handling Investors in a Business Transformation
(52:33) Long Ass-lightning Round: a Profound Lesson From Lanny’s Time at Monster
(55:26) The Hilarious Story About a Marketing Stunt Gone Wrong
(57:07) Lanny’s Parking-related Life Hack
(58:37) Eventbrite’s Finance Team’s Tech Tooling
(01:00:35) The Craziest Thing Someone Tried to Expense




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In this episode, CJ sits down with John McCauley, the CFO of Calendly. From his learnings under the leadership of Frank Slootman and Mike Scarpelli at ServiceNow to his first CFO role at Seismic, and his current position, John shares valuable insights from his career. He gives advice on hiring and getting promoted, why you should consider your value prop to your company, the benefits of seeking healthy confrontation, and why the CFO should take responsibility for overall company performance. From tracking product-led growth in your metrics to debunking the myths of benchmarking, John offers profound insights into what it takes to excel as a CFO in today's evolving software climate. He also explains the role of loyalty in software organizations and why businesses are teams, not families.
If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.
—
SPONSORS:
Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com.
Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC.
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 customized 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.
—
FOLLOW US ON X:
@cjgustafson222 (CJ)
—
TIMESTAMPS:
(00:00) Preview and Intro
(02:02) Sponsor - Mercury | NetSuite
(04:49) What John Learned Under Frank Slootman and Mike Scarpelli
(10:30) A Big Mistake That John Made at ServiceNow
(15:54) John’s Mindset Going Into His First CFO Role
(18:23) Sponsor - Maxio
(21:22) A Lesson on Hiring and Getting Promoted
(24:48) Brand Equity and Calendly’s Viral Coefficient
(28:22) Tracking Product-led Growth in Your Metrics
(32:36) The Changing Climate of Software
(36:16) Creating Value as a Privately Held Tech Company in M&A
(39:12) The Truth About Benchmarking
(42:17) What Makes a Great CFO
(44:41) John on “Moving Slow to Move Fast” 
(47:01) The Role of Loyalty in Business: Team Versus Family
(50:49) The Long-ass Lightning Round: John’s Advice to His Younger Self
(52:20) John’s Finance Software Stack
(53:35) The Craziest Thing Someone Tried to Expense


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In this episode, CJ is joined by Jeff Cooper, the CFO of Guidewire, a publicly traded vertical software company serving the insurance industry. Jeff explains the strategic advantage Guidewire has in owning the control point within a customer's tech infrastructure and how they achieved this. He sheds light on the challenges and benefits of Guidewire's industry-specific business model, including long sales cycles, non-standard fiscal years, and the risks of burning through their market. He also discusses ARR as the most important metric, how he decides on the metrics he reports on, and how to think about the value of professional services within your valuation and value proposition. 
If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.
—
SPONSORS:
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.
Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com.
Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC.
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 customized KPI checklist. 
—
FOLLOW US ON X:
@cjgustafson222 (CJ)
—
TIMESTAMPS:(00:00) Preview and Intro
(01:57) Sponsor - Maxio | Mercury
(04:20) How Guidewire Monetizes Its Business
(08:48) Guidewire’s Strategic High Ground and How They Earned It
(13:53) The Benefits of Owning the Control Point in a Customer's Tech Stack
(16:09) Guidewire’s Long Deal Cycles and Sales Capacity Model
(18:47) Sponsor - NetSuite
(20:09) Navigating Big Deals, Long Sales Cycles, and Seasonality
(22:33) Guiding to ARR
(24:38) The Pros and Cons of Having Fiscal Year End in July
(28:27) Concerns Over Burning Through Your Market
(31:39) Professional Services: In-house Versus Outsourcing
(36:11) The Nature of a Good Partner Ecosystem
(38:44) Communicating the Most Important Metrics
(42:03) Long-ass Lightning Round: One of Jeff’s Biggest Metric Mistakes 
(44:33) The Advice Jeff Would Give His Younger Self
(45:53) Jeff’s Finance Software Stack


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Today, CJ hosts Taylor Holiday, a legend in the e-commerce and D2C (Direct-to-Consumer) world. He is also the CEO and founder of Common Thread Collective, one of the leading marketing agencies for e-commerce brands. Taylor takes us on a deep dive into marketing best practices and shares profound insights from his years of experience in D2C and e-commerce businesses. He talks about bridging the gap between marketing and finance and what marketers often miss about monetization. He explains when to do marketing in-house and when to hire experts, how unit economics and expectations differ in B2C versus B2B, and why it’s so challenging to forecast inventory in e-commerce. Taylor also gives his top tip for anyone starting an e-commerce or D2C business today.
If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.
—
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 customized 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.
Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com.
Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC.
—
FOLLOW US ON X:
@cjgustafson222 (CJ)
@TaylorHoliday (Taylor)
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TIMESTAMPS:
(00:00) Preview and Intro
(02:45) Sponsor - NetSuite | Maxio
(05:28) Bridging the Gap Between Marketing and Finance
09:03) What All Marketers Need to Know
(15:48) In-house Marketing Versus Hiring Experts
(18:35) Sponsor - Mercury 
(21:05) Unit Economics and Expectations in B2C Versus B2B
(25:56) Working With Social Networks in B2C Versus B2B
(28:55) The Four Quarter Accounting Framework for Your Social Media Budget
(31:31) The Challenge of Forecasting Inventory in E-commerce
(35:52) How Gymshark Mastered the Cash Conversion Cycle
(39:16) E-commerce and D2C Companies That Hit It Big
(42:40) How Taylor Made a Fortune Selling Rubber Wedding Rings
(44:43) Takeaways From Taylor’s Years in E-commerce
(49:39) Podcasting as a Marketing Medium
(52:26) Wrap


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Jim Kelliher, the former CFO of PTC, LogMeIn, and Drift, and general CFO legend in Boston, joins CJ to discuss the secrets behind the success of these companies and the lessons he’s learned in his 35-year career. From the importance of product investment to how to navigate IPOs during economic downturns, Jim shares profound insights into how CFOs can drive growth rather than just manage budgets. He explains the importance of investing in product, how to vet budget requests, and how to build a winning team spirit. He also talks about venture capital versus later-stage private equity buyouts and how the growing trend towards the latter is doing what Jim believes to be a disservice to the startup communities they operate within. 
If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.
—
SPONSORS:
Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com.
Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC.
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.
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 customized KPI checklist.
—
FOLLOW US ON X:
@cjgustafson222 (CJ)
—
TIMESTAMPS:
(00:00) Preview and Intro
(02:29) Sponsor - Mercury | Maxio
(05:13) The Six Things That Made PTC Software, LogMeIn, and Drift Succeed
(13:05) The Importance of Investing in Product
(18:26) Sponsor - NetSuite
(19:52) Questions to Ask to Vet Budget Requests
(21:39) Inspiring People to Spend Company Money Like It Was Their Own
(22:55) The Difference Between Being Frugal and Being Cheap
(26:45) How to Learn Negotiation
(28:33) The Importance of Adding High-Caliber People to Your Team
(30:26) Advice for CFOs Mentoring Future CFOs
(32:21) Jim’s Proudest Career Achievement
(33:51) Building a Winning Team Spirit
(40:32) VC Versus PE Buyouts
(48:43) Advice to CEOs or CFOs Vetting Private Equity Sponsors
(55:00) Tips for Timing Your IPO
(58:58) Two of Jim’s Biggest Career Mistakes
(59:50) The Craziest Thing Jim Saw Someone Try to Expense
(1:02:21) Wrap


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