It’s hard to know.
Being CEO is a very, very hard job. It’s constant 24×7 and you never get a break. A chance to sell late stage and make tens or even hundreds of millions is not just a once-in-a-lifetime opportunity … but also a chance to get a mental break.
And yet … if you do sell … that’s it.
Look at this leaked Salesforce M&A target list and go to the bottom — you can see Box and Zendesk are “CEO has no interest”, Workday is “less interested” … yet Marketo, Qlick, etc. are “In Play” and were indeed acquired thereafter.
If all that matters is money, selling for a high price, especially late stage or just post-IPO is the way to go. Especially is SaaS, the odds you can say 10x your valuation again to justify the risk of saying No is … tough.
But life is short, especially where timelines are long. It takes 7–10 years to build anything big in SaaS. And another 10 to really go big. Dropbox just had a monster IPO … but it took 11 years to get there.
You may not have another chance to go even further.