When Shreesha Ramdas left Medallia after a $6.5B acquisition he decided it was time to reinvent.

At his 4th startup Lumber, before writing a single line of code, he hired a sales person and ran 200+ interviews across the industry to understand the real pain points. The interviews gave Shreesha the insight that though payments were a problem, it was neither big enough nor urgent. 

But it was very difficult to hire workers, and even more difficult to retain skilled craft workers. In the U.S alone 41% of construction workers will retire in the next six years, leaving a massive gap in talent and experience. As a big believer in vitamin vs. painkiller, Shreesha is now building where the pain is deepest. 

We discuss what truly needs to happen before building a startup, the foundation that will shape everything that follows. From his days at Yodlee during the dot-com boom to leading StrikeDeck and selling it to Medallia, he is now building again with clarity and intent for one of the most traditional industries: construction.  

But here’s one thing that probably tells you more about Shreesha than the companies he has built and scaled. He said, “My heart beats for other founders. Startup is my world, this community is my tribe.”

0:00 – Trailer
1:04 – Why build tech for Construction industry?
3:54 – 200+ interviews to find the real customer pain
5:05 – Big believer in Vitamin vs. Painkiller
6:25 – The 2 core problems in this industry
7:02 – Repeat founders Know structure better
7:42 – First startup during the dot-com boom
8:29 – Bay Area is Disney Land for tech founders
9:23 – From engineering → sales → marketing
10:37 – Founders should trust the team, above everything
11:55 – The survey company that banned “survey”
12:17 – First startup was all about me; now it’s all about team
13:57 – Dream big, but execute in small steps
15:47 – The cost of speed in startups
16:18 – I’m a marketing-first CEO
17:27 – Hire a salesperson before the product exists
18:17 – Is Founder-led selling good or bad?
19:37 – Mean, lean & go all in
23:55 – Don’t bring humility to storytelling
27:25 – How the story should evolve as startups scale
35:30 – How Lumber will challenge giants in construction
38:53 – Do repeat founders build more in verticals?
43:39 – How to hire right people from traditional industries
44:29 – What wealth unlocked for Shreesha
45:34 – Legacy is moving the industry forward
46:38 – What the next 20 years mean for software founders
49:18 – AI should remove soul-draining work
51:19 – “My heartbeats for other founders”

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This video is for informational purposes only. The views expressed are those of the individuals quoted and do not constitute professional advice.

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