An Insider's Guide After $2B of M&A with Serial CFO Steve Love of Sift, Dialpad, and Heap

In this conversation, Steve Love, a seasoned CFO with over $1 billion raised from VCs and $2 billion in M&A transaction experience, pulls back the curtain on high-stakes M&A. Love shares his insights from overseeing complex acquisitions like Heap's purchase of a complementary "session replay" company and Heap's eventual sale to ContentSquare.

He candidly discusses navigating challenges, aligning stakeholders, prepping for diligence, and making strategic M&A decisions as a CFO. Whether you're a CFO, finance professional or simply M&A-curious, Love's tactics for evaluating targets, modeling forecasts, negotiating terms, and executing integrations provide a rare behind-the-scenes look at what it really takes to architect successful transactions.

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🔗 Links

Check out Sift: https://sift.com/

⏲️ Timestamps:

(00:00) Preview

(01:15) Intro

(02:23) Immad’s Journey to founding Mercury and being a serial entrepreneur

(02:37) Immad’s learnings after founding three startups

(06:54) Learnings from being a YC partner and angel investor

(08:54) What gets Immad excited about investing

(10:17) Why Series A vs seed stage investing

(12:18) Building the banking solution

(13:49) The moment when Immad knew Mercury was the right thing

(16:12) How interest rates affect Mercury

(18:48) Silicon Valley Bank collapse and what was happening at Mercury

(23:50) SVB failed, why is Mercury safe?

(24:00) Mercury Vault’s inception and increasing FDIC insurance to 3 million

(25:56) Would Immad do anything differently going back to the SVB collapse?

(27:41) How Mercury’s team was able to remain calm and adapt

(29:21) Launching new products within a startup: product innovation

(31:12) Having a longterm mindset when launching new products

(33:49) Thinking about product launches internally like they’re startups

(36:37) Breadth vs depth in a market

(40:30) Something about Mercury a lot of people don’t know today

(43:50) Number one piece of advice for founders

(44:26) Wrap

Subscribe to this season of Turpentine Finance, where our guests speak candidly about big business inflections, market curveballs, and how they approach decision-making to tease out tactics and mental models you can use when the pressure is on.

You’ll hear stories from Instacart, Mercury, OpenAI, Andreessen Horowitz, Netflix, Runway, and more. Topics frequently touched upon M&A, Market Downturn, Macro, PMF, Fundraising, Financial Forecasting, Headcount, Equity.

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Turpentine Finance is a part of the Turpentine podcast network. Learn more: www.turpentine.co

This show is produced by Turpentine: a network of podcasts, newsletters, and more covering technology, business, and culture, all from the perspective of industry insiders and experts. We’re launching new shows every week, and we’re looking for industry-leading sponsors - if you think that might be you and your company, email us at [email protected]