Downtime, Deals, and Dad Life | The Masset Journal (entry #6)

First downtime, new hires, Stripe wins, and preschool interruptions. A real week in startup life from the founders of Masset.

April 14, 2025

Hey there — Tyler and Ben here.

This week was a bit of a first for us. First real outage. First time a kid screamed during the podcast. First time we got paid mid-recording. Honestly, kind of a milestone week.

Here’s what’s going on at Masset:

The Security Update That Took Us Down (Briefly)

Tyler here. Most of my week was spent on pen test remediation — part of our push toward SOC 2. For the unfamiliar, it’s not “SOC 2 certified,” it’s “SOC 2 reported.” You don’t pass or fail, you just demonstrate you’re serious about your security controls. And we are.

The good news: our pen test came back pretty clean.
The bad news: I made a security tweak that temporarily broke our login system.

What happened:

  • I updated how we manage session cookies.
  • Everything passed local and staging tests.
  • Deployed it at 4:30pm (technically after hours, right?).
  • Boom. Login system down for 35 minutes.

Not our finest moment, but not the end of the world either. It was our first real downtime in 18 months — and it was short. We fixed it quickly, learned from it, and updated our systems. Shoutout to anyone who was affected and stayed patient.

And if you're ever curious, our public status page is at status.getmasset.com. Hopefully, you won’t need it again for another 18 months.

Hiring, Selling, Onboarding… All at Once

Ben here. This week has been a classic founder juggling act.

Here’s what a typical day looked like:

  • Ran interviews for our new BDR (or SDR — Utah folks seem to prefer that term?) role.
  • Sent out a dozen texts to my network looking for referrals.
  • Signed a new customer contract.
  • Ran training calls with new clients.
  • Updated website content.
  • Reviewed unsolicited sales pitches (some good, some not).
  • Set up demos and supported onboarding.

Also, a fun moment — while we were recording this week’s video, Stripe pinged us in Slack: a new customer payment came through. Always a nice morale boost.

(Pro tip: integrate Stripe with Slack and add a 🔥 emoji to each one. It's silly, but it works.)

What's Next

Here's what we're focused on right now:

  • Hiring a strong BDR to help us scale outbound.
  • Finalizing SOC 2 work.
  • Wrapping up HubSpot integration.
  • Prepping for Salesforce next.

Also: continuing to support our customers and grow the business — while sometimes dealing with preschoolers screaming just outside the home office door.

A Final Thought

One thing we both love about the current work-from-home world: kids walking in, yelling in the background, and nobody blinking an eye. It’s refreshing. A reminder that life is happening right alongside the work — and that’s just fine.

Until next week,
Tyler and Ben