Run the Numbers: Taking Criticism Like a Pro

Guest: Ambereen Toubassy (CFO, Airtable)
Host: CJ Gustafson
Release Date: March 13, 2025

Episode Overview

This episode of Run the Numbers explores how top tech CFOs navigate tough investor feedback, build strategic advisory networks, and make standout contributions at high-growth startups. CJ Gustafson interviews Ambereen Toubassy, CFO of Airtable, on her journey from banking and hedge funds to operating CFO roles, tackling topics like negotiation empathy, scaffolding weaknesses through advisors, the lessons from ambitious moonshots like Quibi, and why specificity and curiosity are vital for effective leadership in finance.

Key Discussion Points and Insights

1. Negotiation Empathy: Sitting in Every Seat

[07:13–10:48]

• Ambereen’s background: From investment banking to hedge funds to operating company CFO, she’s “been in all three seats” (advisor, investor, operator).
• Empathy in negotiation: Having “viscerally” sat in every seat gives her unique insight into what each party is seeking.
  • Quote [09:51]:
    “A win for them cost us nothing, so it's not like a win for them was a loss for us. It was a perfect situation where it cost me nothing, gives you something, and that's sort of like the perfect win-win.” — Ambereen
• Growing the pie: Tech and SaaS allow for “bigger pies” versus zero-sum legacy industries.

2. Taking Criticism and Investor Feedback Like a Pro

[10:48–16:35]

• CJ asks about dealing with investor critique, referencing the “Succession meme” of unsolicited advice.
• Ambereen’s strategy: She intentionally dials down defensiveness, “actively invites” feedback and reframes it as coaching.
  • Quote [13:23]: “I consciously kind of let go of that. Like, I consciously, I'm like, oh, my body just went into that emotional state. I'm going to dial that down, dial up the curiosity and like, lean in and really listen.” — Ambereen
• Private vs. public company dynamics: Frequency and intensity of feedback differ.
• Leaning into curiosity rather than defensiveness.
  • Quote [16:35] (CJ): "If you're getting feedback from someone who has seen more data points than you... you're kind of getting this cheat code if you're willing to listen."

Example—Applying Feedback to SaaS Renewals

[15:15]:

• Ambereen prioritizes sustainable growth (“let’s do a 6,000 seat renewal, not 10,000”) to protect Net Dollar Retention (NDR) over short-term wins.

3. Emotional Self-Regulation in High-Feedback Environments

[23:16–24:10]

• Meditation and self-awareness: Ambereen uses mindfulness to recognize physical cues of tension, acknowledging emotions internally or in meetings to foster a culture of curiosity.
  • “If your heart rate goes higher, if you get a clenching in your stomach... it's actively sort of reminding yourself from the rational side of your brain: there’s no reason to tense up.”

4. When to Bring Founders into Investor Meetings

[24:30–25:51]

• Strategic deployment of founder time: Reserve CEO’s presence for vision/technology-centric meetings; CFO handles metrics and business operations.
• Translating macro (investor sentiment) to micro (team action).

5. Scaffolding Weaknesses: Using Advisors Strategically

[26:07–30:57]

• “Scaffold your weaknesses” (credit: Jim O’Gorman)—identify blind spots and augment them with external or internal expertise.
• Examples:
  • No need to hire bankers for fundraising (her expertise), but brought in top advisors for pricing and packaging overhaul.
    • “We did not use banks or advisors to do those fundraisers because I've done so many... on the other hand, we also were working through a pretty big overhaul of pricing and packaging... for that, we actually brought in Simon Kutcher...”

6. When “Paying Up” for Advisors is Worth It

[30:59–33:51]

• CJ’s theory: Sometimes you should opt for the highest-fee advisors/law firms if the value justifies it.
• Ambereen’s response: “I want to measure the value I will get from something and then I want to pay less than the value... you can buy something cheap and get no value, in which case you overspent.”
• Context matters: For high-stakes deals (e.g., selling the company), pay for top-quality advisors; for small “tuck-ins,” basic providers suffice.

7. Choosing the Right Advisors and Red Flags

[33:51–39:06]

• It’s about the person, not the firm: CFOs share which partners (not just firms) to hire.
• Caution: Big firms may provide standardized diligence, which isn’t always right for small/unique deals. Bring in advisors who “play the game you’re trying to play.”
  • Memorable story [35:36]: Large firm missed a cash reconciliation red flag in a small deal because it wasn’t usually a top priority in their standard methodology.

8. The Power of Specificity in Leadership (“In the particular is contained the universal”)

[39:06–45:22]

• Quoting James Joyce: Importance of specifics, whether in life lessons or business (illustrated via a tennis anecdote from her daughter).
  • “The abstract ‘she’s a great tennis partner’ didn’t capture the specificity of why she’s a great tennis partner.”
• Translating to business: Specific metrics, insights, and action steps drive real impact in planning and accountability.
  • “It’s making it real... we can go to post-sales and walk them through the ten specific customers where they need to put in effort, as opposed to just saying, ‘hey, renewal rate should be 94%.’”

9. Back-of-the-Envelope Math & Seeing the Big Picture

[45:22–46:45]

• Top CFOs can do fast, accurate estimation because they’ve “been in the guts of the business.”
• Encourages teams to disconnect from Excel details and double-check logic from a “big picture” viewpoint.

10. Moonshots and Leadership Lessons from Quibi

[46:45–54:29]

• Why join Quibi? Drawn by audacity, creative mission, and Jeffrey Katzenberg’s passion.
• Culture: High-performing, mission-driven team—“people who wanted to do more when people said we were doing something stupid and impossible.”
• Failure handled responsibly: Chose to return capital to investors and cared for employees/stakeholders, rather than multiple pivots.
• Airtable discovery: Used and championed at Quibi, proving its value and creative empowerment in practice.

11. Lightning Round—Real-World Insights and Fun

[55:11–58:48]

• Biggest screw-up: Losses as a portfolio manager—memories are vivid and lasting.
• Advice to younger self: “Time flies, but it’s never too late to do something different... Don’t overthink moves; some serendipity is good.”
• Finance tech stack: Workday (HRIS/Financials), Salesforce, Stripe, CaptivateIQ, Airtable (“replaced 400 other applications with Airtable internally!”).
• Wildest expense report attempt: Someone tried to expense a used car.

Notable Quotes & Memorable Moments

• On Negotiation Empathy

  “A win for them cost us nothing. So it's not like a win for them was a loss for us. It was a perfect situation where it cost me nothing, gives you something, and that's sort of like the perfect win-win.”
  — Ambereen [09:51]

• On Receiving Feedback

  “I'm going to dial that down, dial up the curiosity and really listen... It’s all about making sure I'm in the mode of curiosity.”
  — Ambereen [13:23]

• On Advisors

  “It's a pretty tight network... Usually I’ll say, this applies to me as well as others: very seldom will someone say ‘which firm do you use,’ it’s more ‘which partner do you use?’ To me the person is much more important than the firm.”
  — Ambereen [34:18]

• On the Power of Specifics

  “It’s making it real ... as opposed to just saying, ‘Hey, renewal rate should be 94%.’ Which again makes it harder for people to know what should I do differently?”
  — Ambereen [44:08]

• On Failure

  “It was a moonshot idea, it wasn’t successful. I think the fact that we always knew it was going to be difficult... The 300 people that it attracted were a specific DNA of people ... people who wanted to do more when people said we were doing something stupid and impossible.”
  — Ambereen [47:31]

Timestamps for Major Segments

• Negotiation Empathy: [07:13–10:48]
• Handling Criticism and Investor Feedback: [10:48–16:35]
• Emotional Regulation, Curiosity, and Feedback: [23:16–24:10]
• Founders in Investor Meetings: [24:30–25:51]
• Working with Advisors, Scaffolding Weaknesses: [26:07–30:57]
• Advisor Fees & Value: [30:59–33:51]
• Choosing Advisors, Red Flags: [33:51–39:06]
• The Universal in the Particular (Specificity): [39:06–45:22]
• Back-of-the-Envelope Thinking: [45:22–46:45]
• Quibi Moonshot, Failure & Responsible Leadership: [46:45–54:29]
• Lightning Round: [55:11–58:48]

Tone and Style

• Conversational, candid, self-deprecating humor (“I know the best CFOs are true business leaders … sometimes I find myself watering the plants and taking out garbage in the office.” — CJ).
• Emphasis on vulnerability, honesty, and practical, tactical advice.
• Focused on specifics, real stories, and actionable insights.

In Summary

Ambereen Toubassy’s wisdom as Airtable CFO demonstrates how time spent in every seat—advisor, investor, operator—powers world-class negotiation, empathy, and leadership. Her approach to feedback, strategic use of advisors, and insistence on specificity exhibit the playbook for ambitious tech finance leaders. The episode is loaded with candid anecdotes, tactical finance advice, and the human side of C-suite decision-making.

A must-listen (or read) for anyone navigating the intersection of finance, technology, and high-growth startups.