Ep 19: Gmail Email Label Hell

Welcome back to The Nights & Weekends Podcast, where Craig Hewitt and Ken Wallace are shedding light on the journey to bootstrap real businesses.

This Week

This week, Craig gives an update on his progress bringing his new virtual assistant (VA) up-to-speed. Craig has a variety of processes that are crucial to delivering a high quality of service to PodcastMotor clients. It has become really clear that it will take a slow and steady approach to bring her fully into all of those processes. Slow and steady wins the race.

Ken gives updates on MastermindJam. After spending a few days untangling an email automation mess* of his own making, Ken reflects on the growing customer support needs of this business. He’s outgrowing Gmail labels, so either he needs to figure out a better way to systemize his interactions with his customers, or drastically cut out all of the complexity and go back to a much simpler system.

Which brings up the question: How early is too early to add customer helpdesk, support and/or CRM software into a new startup? Surely the pace of revenue growth is a factor in that decision, but after that, it seems to be a bit of a judgement call. And it’s weighing on Ken’s mind as he wakes up to Inbox OMG after going to bed with Inbox Zero.

In addition, Ken is focusing on the customer experience. He’s learning a lot from customer feedback, and has formed a plan to address these critical needs:

  1. customer scheduling issues
  2. improvements in the mastermind match algorithm (oy, bitmasks)
  3. changes to the customer onboarding experience


One thing’s for certain: it’s imperative that Ken and Craig find a way to scale and grow these businesses. Or, what’s the point?

Craig truly needs to stay focused on growth and scale without adding more chores to his own plate. It’s a tough nut to crack, but he can do it.

Ken needs to find a way to monetize MastermindJam beyond the current model. The match fee is great at ensuring that only the most committed entrepreneurs are applying to be matched, but there has to be something more for this service to continue — more avenues to add real value, solving real problems, to grateful customers, in a repeatable, scalable fashion, in exchange for recurring dollars.

If not, then Ken will have some tough decisions at the end of Q3 going into Q4, as he’ll need to decide if it’s worth his time to continue to pour resources into what may be an online business money pit. Is this investment property, or a waste of time? Too early to tell.


Q3 Accountability Checkup

Finally, Ken and Craig decide to once again put a stake in the ground and make a decision to be accountable to a revenue goal in the next three months. Listen closely for details so you can hold us accountable, too.

Let us know in the comments if these goals seem far-fetched or very doable from all you’ve heard, taking into consideration your own experience.


Introducing the Nights & Weekends Podcast drinking game!

Head over to the website to see a candid animated gif taken from this week’s recording session. Watching this gif loop, it looks like there’s some secret drinking game Craig and Ken are playing — where, if one person drinks, everyone has to stop talking mid-sentence and drink as well.

Leave us a note in the comments of the things you hear us saying over and over. It’s those kinds of things that make a great drinking game. We’ll announce the rules to the new drinking game next week.

2015-07-15 17_52_08 Ken and Craig Drinking Stuff

Thanks so much for listening!


*Note from Ken: I mentioned that Drip had no way to move customers one-by-one from one campaign to another, which, as I’m listening to this episode I realize is a very misleading statement. In Drip, you can click on a subscriber and view what campaigns they are a part of, and remove them from their current campaign. On that screen: no, you can’t move them to a different campaign. However, on a different screen, Drip does have a bulk update feature that lets you type in a single customer email address, a list of addresses, or specify a customer segment based upon filters, then perform any action you choose, such as: moving to a different campaign, adding an event, tag, or custom field, or send a one-off email. It’s really a versatile software package, I just chose to do it the harder way: via the API. I made my changes programmatically via the API for many of my customers, so I could easily sync those actions with my software’s database. Your situation will likely be simpler, so be sure to take a look at Drip’s documentation and help videos to get a more complete picture of Drip’s capabilities.


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