WP Engine

15 statements across 10 episodes · 9 bullish · 1 bearish · 2 people on the record · first statement Mar 23, 2021 by Rob Walling · said 34 times in 19 episodes since 2020 · across every show →

Mentions by year

brought up most by Rob Walling (32), Matt Wensing (2)

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2025 2 mentions in 1 episode
2024 16 mentions in 6 episodes 3 per episode
2023 9 mentions in 6 episodes 2 per episode
2021 6 mentions in 5 episodes 1 per episode
2020 1 mention in 1 episode

every mention, scene by scene, with the transcript →

Everything said about WP Engine, oldest first

Mar 23, 2021 positive
Disclosure
Walling discloses his first angel investment check went to WP Engine
“It was about a decade ago, I believe, I was able to write my first check, which was to WP Engine, and, you know, it was a small check, and a lot of them until I saw drip were small”
Rob Walling Mar 23, 2021 ▶ 24:00 Episode 541 | Rob Solo
Jul 6, 2021 bullish
Disclosure
Rob Walling was an early angel investor in WP Engine
“It's either angel investing, because I was an early investor in WP Engine and several others that have done reasonably well, or crypto currency.”
Rob Walling Jul 6, 2021 ▶ 2:54 Episode 557 | Investing for Founders
Apr 4, 2023 positive
Disclosure
Walling: Life-changing wealth came from WP Engine angel investing and exits
“The life-changing income that I've received has been from selling my own companies and from angel investing in companies like WP Engine and a few others that had these massive returns on my investment or on my time, and the tax advantages were there as well.”
Rob Walling Apr 4, 2023 ▶ 38:15 Episode 655 | Seat-Based Pricing, Can Churn Be Too Low? and More...
Apr 4, 2023 positive
Assertion Supported
Walling: Drip secured 11 commitments and WP Engine 40 before coding
“With Drip, I got 11 yeses. With WP Engine, Jason Cohen got 40 yeses before he started coding.”
Rob Walling Apr 4, 2023 ▶ 12:07 Episode 655 | Seat-Based Pricing, Can Churn Be Too Low? and More...
Apr 18, 2023
Assertion Supported
Walling: Jason Cohen paid consultants' hourly rates to validate WP Engine
“I know that Jason Cohen, when he was vetting WP Engine, he would actually pay consultants or agencies, or he would offer to pay. He's like, I know your rate is a hundred dollars an hour, And I'll pay you know, for a half hour or for a full hour of your consult…”
Rob Walling Apr 18, 2023 ▶ 21:04 Episode 657 | Concierge Onboarding, Building a Great Brand, and M...
Aug 29, 2023
Assertion Partly supported
Rob Walling: Jason Cohen obtained 40 customer pre-commitments validating WP Engine
“I had modeled my approach after Steve Blank's original customer development, but realistically, more so after Jason Cohen's validation or pre-validation of WP Engine. And he talked to a lot of people, and he got 40 yeses.”
Rob Walling Aug 29, 2023 ▶ 26:17 Episode 676 | Exit Valuations, Choosing Between Ideas, and More L...
Feb 13, 2024 positive
Disclosure
Rob Walling's $20,000 WP Engine angel check is his third-best asset
“When I scraped together, you know, a couple, 20 grand, I think, which was an enormous amount of money for me at the time. To write Jason Cohen a check, and I was honored to be part of it, and it paid out a tremendous, tremendous payout for me, and it's probabl…”
Rob Walling Feb 13, 2024 ▶ 10:51 Episode 700 | Playing the Long Game
Apr 16, 2024 positive
Assertion Not checkable as stated
Rob Walling's WP Engine angel exit paid cash for a house
“When WP Engine had, ah, what I think was considered a private equity kind of growth round in, in 2018 or 19, we got bought out. And that was enough money that we could pay cash for our next house”
Rob Walling Apr 16, 2024 ▶ 21:37 Episode 709 | The 7 Greatest Investments of My Life
Apr 16, 2024 neutral
Assertion Not checkable as stated
Rob Walling wrote his first unaccredited angel check to WP Engine
“That was the first angel check we ever wrote. In fact, we were not accredited investors.”
Rob Walling Apr 16, 2024 ▶ 23:03 Episode 709 | The 7 Greatest Investments of My Life
Oct 15, 2024 negative
Opinion
Walling: WordPress has shown it is an aggressive, unfriendly platform
“Given that WordPress has shown that they are going to be aggressive, not making themselves out to be a friendly platform right now.”
Rob Walling Oct 15, 2024 ▶ 17:27 Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adve...
Jun 10, 2025 neutral
Disclosure
Walling: Holds 224 B2B SaaS investments, dozens at seven or eight figures
“I'm invested in 224 B to B SaaS companies. Dozens of them are doing seven or eight figures, and, you know, there's WP Engine, which is, what do we think the worth of them is a billion.”
Rob Walling Jun 10, 2025 ▶ 17:45 Episode 778 | Pricing Pilot Projects, Niching Down, Skipping Stai...
Jan 27, 2026
Disclosure
Cohen: WP Engine bootstrapped for two years before raising $1M
“When we raised money, which wasn't for two years, because originally the idea was to bootstrap it again, it was the fourth bootstrap company. It's just right. But even then we only raised a million dollars. It's not exactly like earth shattering quantities of …”
Jason Cohen Jan 27, 2026 ▶ 30:40 Episode 817 | Bootstrapping in the Age of AI with Jason Cohen
Jan 27, 2026 positive
Assertion Not checkable as stated
Cohen: WP Engine's growth permanently inflected after 2012 pricing changes
“The pricing was already pretty good, but we had some revelations talking to customers, and Hearing some stories or some revelations where we reset the prices, not dramatically, just like certain things in 2012. And that's when we really took off. That's like w…”
Jason Cohen Jan 27, 2026 ▶ 31:24 Episode 817 | Bootstrapping in the Age of AI with Jason Cohen
Jan 27, 2026 positive
Disclosure
Cohen: WP Engine spent tens of millions expanding into enterprise campaigns
“When WP Engine first started, we were only for like small business, maybe medium sized. A lot of times it was going through freelancers, sometimes direct. And sure, four or five years in, we saw some more appetite from larger companies, but not for their homep…”
Jason Cohen Jan 27, 2026 ▶ 25:20 Episode 817 | Bootstrapping in the Age of AI with Jason Cohen
Jan 27, 2026 positive
Disclosure
Walling: Angel investment in WP Engine paid cash for his house
“That bought our house. Paid cash for our house.”
Rob Walling Jan 27, 2026 ▶ 3:01 Episode 817 | Bootstrapping in the Age of AI with Jason Cohen
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