Actually, I wonder if the creator of WWWBoard/FormMail/etc achieved that. It certainly would've been well earned. His stuff was everywhere (I used them a lot too).
Check out GlobalSigns Cloud SSL product if you want a cert that can mix wildcards with top level SANs....not free but....https://www.globalsign.com/en/cloud/
I'm a single founder of a B2B SAAS - took 3 years to get to 10K MRR. From Jan 1 of this year MRR has grown from 10K MRR to 27K MRR. Likely due to a combination of better product market fit, getting some very marquee name clients and price increases. Finally quit my full time gig in April - never looking back I hope!