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5 Ingredients for the Perfect Investment | Jeff Horing Interview

5 Ingredients for the Perfect Investment | Jeff Horing Interview

12 segments available

Jeff Horing, founding partner of Insight Partners, shares his approach to building one of the world's largest venture capital firms. In this rare interview, Horing discusses Insight's unique one-fund strategy, systematic sourcing process involving 60+ people, and how they've graduated 16-18 fund managers who started their own firms. He breaks down the "college-level math" behind evaluating software businesses, explains why gross retention matters more than net retention, and reveals his five ingredients for the perfect investment. The conversation covers Insight's evolution from growth equity to buyouts, their operational support platform with 130 people, and Horing's contrarian views on AI's impact on software companies. A masterclass in institutional venture capital strategy and execution. Timestamps: 00:00 Intro 15:40 Five Ingredients of Perfect Investment 20:14 One Fund Strategy 28:02 Sourcing Evolution & Strategy 44:00 What Makes a Great Sourcer 55:14 AI Applications & Late Stage Deals 1:00:12 Pattern Recognition & Training 1:08:05 Scaling Judgment Without Breaking 1:29:01 AI Impact on Software 1:36:28 Drive to Win 1:38:53 Next Decade of Insight 1:41:40 The Kindest Thing #VentureCapital #PrivateEquity #SoftwareInvesting #InsightPartners #GrowthEquity #StartupFunding #TechInvesting #InvestmentStrategy #AI #SaaS #stocks #investment Presented by Ramp: https://ramp.com/business-cards?utm_s Sponsored by AlphaSense and Ridgeline: https://www.alpha-sense.com/invest/ https://www.ridgelineapps.com/ ****** Patrick O'Shaughnessy is the CEO of Positive Sum. All opinions expressed by Patrick and podcast guests are solely their own and do not reflect the opinion of Positive Sum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of Positive Sum may maintain positions in the securities discussed in this podcast. To learn more, visit psum.vc

Segments Timeline

1
0:00 - 15:42
15:42 duration3218 words

Intro

"I'm a big fan of the value prop. I want to hear the entrepreneur explain how they're generating real value for the customer. In fact, I I think when I look at what makes for the perfect investment, I ..."

2
15:42 - 20:15
4:32 duration967 words

Five Ingredients of Perfect Investment

"uh I then kind of look at in fact I I think when I look at what makes for the perfect investment I have kind of thought about the the five ingredients to me all that's here >> perfect investment so va..."

3
20:15 - 28:03
7:48 duration1726 words

One Fund Strategy

"you have strong beliefs about it. So maybe describe why it is this way and and the trade-offs. I'll give you a couple angles on it, but first I was lucky enough to get my first job and it was a lot of..."

4
28:03 - 44:00
15:57 duration3469 words

Sourcing Evolution & Strategy

"strategies or not um as businesses. But but let's start with sourcing. When I wrote the original business plan, which is not tremendously different than today, uh, which is a longer story, but I was l..."

5
44:00 - 55:14
11:13 duration2322 words

What Makes a Great Sourcer

"like the merely good? >> It's got a lot of classic sales skills, which is hunger, winning, probably lack of self-awareness. Meaning like you'll make a phone call to anybody and not care. >> Yeah. >> A..."

6
55:14 - 1:00:13
4:59 duration1069 words

AI Applications & Late Stage Deals

"had zero revenue. So, >> it's a big price, but, you know, we loved everything we saw, including team. Uh Monday it was an interesting company but not the most obvious funded company. It was you know p..."

7
1:00:13 - 1:08:06
7:53 duration1657 words

Pattern Recognition & Training

"that just sticks with them in their later life and I think it probably makes them look good to the peers that they have that didn't have that culture. If we're building like a like a Madden player tha..."

8
1:08:06 - 1:29:04
20:57 duration4183 words

Scaling Judgment Without Breaking

"like every industry but ours was considered to be better as they got bigger. Like for some reason this type of investing, tech investing was like, "No, we want you to be a cottage industry where the s..."

9
1:29:04 - 1:36:29
7:25 duration1435 words

AI Impact on Software

"and I'm not like the technology ology wizard in the firm by any stretch. But I I we were already doing vision deals and I could see language was next. I was like, imagine if you can automate vision an..."

10
1:36:29 - 1:38:57
2:27 duration498 words

Drive to Win

"don't care about other beating other people >> so much as just satisfaction in my own success in winning. So it's a different kind of drive than I think other people get, which is I I have friends who..."

11
1:38:57 - 1:41:41
2:44 duration570 words

Next Decade of Insight

"crazy ambitions to expand the business beyond what we're really good at. And just I think this is a just kind of we'll we'll absorb what we think are great deals, but the bar has never been higher. Si..."

12
1:41:41 - 1:43:24
1:43 duration307 words

The Kindest Thing

"of the goodness of their heart, not out of their own self-interest. And I'm somewhat fortunate not to have that many situations where I've needed that help. But I I guess as others have said in this m..."