Nov 22, 2017 · 26m · 20vc
20VC: Why Strategic Investing Is Slow Motion M&A, Why Valuation Is The Hardest Element of M&A & What Determines Between Cash vs Stock Deals with Chad Richard, SVP of Business & Corporate Development @ Yelp
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In this episode of The 20 Minute VC, host Harry Stebbings interviews Chad Richard, SVP of Business and Corporate Development at Yelp, exploring strategic M&A, valuation complexities, and deal structuring. Chad shares lessons from Apple and Yelp on how partnerships, minority investments, and executive alignment drive successful tech acquisitions.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 29.9% of the talking time here. How this is scored →
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Chad politely offers a counter-perspective to investor Rishi Gaug's quote cited by Harry, reframing the idea of building an M&A target pipeline into cultivating operational business partnerships.
Hardest push from Harry ▶ 12:37 Harry presses for internal corp dev approval detailsHarry interrupts to redirect the narrative back to Yelp's precise internal sign-off flow after Chad gives a higher-level answer about investment philosophy.
Biggest teaching moment ▶ 17:45 Chad explains liquidity and valuation risk profilesChad breaks down the financial and psychological differences for founders taking public stock with instant liquidity versus highly valued private stock subject to market valuation swings.
Harry holds his own ▶ 17:23 Harry contrasts public incumbents against mega-private unicornsHarry shows strong subject matter knowledge by bringing up specific industry examples like Airbnb and Uber to contrast private mega-balance sheet acquisitions with public market dynamics.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Chad Richard's Early Background and Entry into Startups | 3 | 4 | 1 | 1 | Harry asks Chad about his background and entry into tech M&A at Apple, prompting a detailed discussion on product-driven M&A versus revenue acquisition. Harry demonstrates solid host context by contrasting Apple's methodology with traditional financial acquisition models. | |
| Building the Deal Pipeline through Partnerships at Yelp | 2 | 3 | 0 | 0 | Harry introduces the topic of Yelp's deal pipeline, and Chad details how combining business development partnerships with corporate development replaces guesswork with real operational metrics. | |
| Strategic Investments, Partnerships, and Founder Alignment | 4 | 3 | 1 | 1 | Harry raises perceptive questions regarding founder anxieties around strategic corporate investments and exclusivity risks. Chad validates Harry's point, offering nuanced advice on timing strategic investments in later funding rounds. | |
| Yelp's Internal M&A Decision-Making Workflow | 4 | 2 | 0 | 2 | Harry presses Chad for granular details on Yelp's internal decision-making process from corporate development approval to sign-off, introducing the term 'slow motion M&A'. Chad adopts the framing and breaks down internal stakeholder alignment. | |
| Valuation Challenges, Retaining Talent, and Cash vs. Stock Structure | 6 | 4 | 1 | 1 | Harry demonstrates strong financial acumen by asking how deals are valued without P/E ratios and contrasting public acquirer stock deals with private mega-unicorns like Uber and Airbnb. Chad explicitly commends Harry for zeroing in on one of the hardest aspects of M&A. | |
| Founder M&A Strategies and the Role of VCs | 5 | 3 | 1 | 1 | Harry cites investor advice from Rishi Gaug regarding startup M&A target pipelines and asks about VC involvement during deals. Chad gently reframes the advice around business development partnerships while highlighting the value of un-emotional VC advisors. | |
| Quickfire Round with Chad Richard | 2 | 1 | 0 | 0 | Harry conducts a standard quickfire round covering books, blogs, and day-to-day challenges, which Chad answers cooperatively and succinctly. |