Discovering the Minimum Path to Awesome with Rob Walling

Rob Walling is the author of A Developer’s Guide to Launching a Startup. He co-hosts Startups for the Rest of Us, a popular startup podcast I really enjoy, hosts MicroConf, a self-funded startup conference. He also owns HitTail and Drip.

When we started the Things That Don’t Scale project, the first person I thought of interviewing was Rob Walling, the founder of Drip.

Anyway, Drip is an app that helps you do marketing automation to increase conversion for startups and software companies. It’s excellent -- easy to use and gets you results out of the box… But what stands out for me? Is what the software does not do.

As part of Drip’s onboarding, Rob and his team hand-craft a custom email sequence for their customers. For free.

This, in my experience, is what keeps people from reaping the promises of marketing automation. It’s also the hardest part. The one that cannot be automated.

In this interview, Rob talks to us about:

If you’re trying to figure out your onboarding to increase conversions and reduce churn, this interview with Rob will be overwhelmingly useful to you.

Here’s Rob --

“Discovering the Minimum Path to Awesome” with Rob Walling, as told to Chiara Cokieng

At what point during the process does your trial user get their rush?

When they realize,

“Holy shit. This is really cool?”

For HitTail, a keyword tool, that Minimum Path to Awesome or MPA is as soon as they see keyword suggestions. So how can I get them there as easily as possible? For HitTail, it’s getting them to link to Google Webmasters as soon as possible.

For Drip, a marketing automation tool, I thought the MPA is someone from their email list purchasing something. But what I’ve learned from talking to a lot of customers is that it’s getting their first subscriber. That’s a big rush.

How do you discover the Minimum Path to Awesome?

Well, what is the headline of the landing page?

Because that headline is the value I am providing to customers. You want to deliver that value as soon as possible. To discover it, you can do it for your first customers first. And as soon as you have your first case study, you can use that specific result to communicate the value they’ll get.

So do it for your first customers, document that process, then break it down into steps. That’s your Minimum Path to Awesome.

The simpler it is, the better.

But Drip’s is a complicated, 4-step process. This is where it ties into concierge…

Can you do it for them?

If you only have one step, ask, can you do this for them?

For Drip, we installed the Javascript on their website. Literally, our support guy did it for up to 500 customers.

We also help them build an email course. And we do that for free as long as someone has some content. Even if they don’t, we hire a professional copywriter to do it for them. And we do it at cost. We don’t mark it up. I don’t want to profit there.

I want customers to stick around.

We originally tried to charge for it.

I was gonna charge $299, dropped it to $99, then decided to run a test. We’ll do it for free, then if we felt overwhelmed, we’ll go back to charging.

That was 18 months ago, and we still do it for free today. Yes, we do create courses that people don’t use and they cancel… But most customers are really happy with it.

The small fee pales in comparison to the lifetime value. You can get so many customers when you do it for free.

It sounds like it takes a ton of time. But we have streamlined much of it. My support guy does it in less than half an hour to an hour.

It doesn’t scale infinitely. But at this stage? It scales.

When we started doing it for free, we started getting double digit user growth for Drip. So ask yourself,

Can I do this for them?

What our customer onboarding process looked like when we first launched?

Today, it’s 3 different things.

One, we send out automated, behavior emails. Two, we have a concierge service to build an email course for them. Three is the UI element. We have a banner, a progress bar, above the app that sits there until you complete your three steps.

But I hand onboarded people at first.

I sent emails manually from Gmail. I recorded one-off screencasts. I even did screensharing and did it for them. It was all manual. I did it for up to 25 paying customers.

It was lots of work. I was spending 20 hours/week doing this. We were making $1000/month.

But once we’ve done enough of that, we started looking at emails and screencasts. The patterns became obvious, that yup, this is what people need to do, and we just translated them into emails.

Absolutely do manual at first.

You’re not just trying to get them onboarded… You’re trying to get their objections. There’s that whole Customer Development thing going on.

There’s more value to doing manual at first than just onboarding.

That said, we haven’t taken away the concierge service away from our onboarding. We don’t see any indications that we should.

Perhaps at scale… Like 5000 trials/month? Perhaps, we’ll stop doing it. But I actually think it might still be worth it.

I see 2 really common mistakes people make in marketing automation.

One is trying to write like a corporation with fixed email templates.

Any marketing automation I do is from me, Rob, the founder of Drip. It’s very personable. It’s like talking to me. Feel free to reply anytime. Sincerely, Rob.

I’m not acting like we’re some big company and using the Oracle tone of voice. The worst is ecommerce with their sexy images.

For people doing a small software thing like this, I don’t know anybody who gets better results from using HTML templates.

Second is not communicating with their list enough and the list gets cold.

Finding new customers is so expensive.

Maintaining people on subscription is infinitely cheaper.

The interesting thing with subscriptions is you basically have to resell every 30 days.

So with SAAS, your goal is to build relationships.

For example, we get a lot of feature requests from both prospects and customers. We have power users we know by name. When they request things, we prioritize them. We know they’re on point and make good feature requests.

When we raise prices, we email everyone that we’re raising them, but you’re still getting the old pricing. It’s definitely good to let customers know we’re doing that for them.

We also let them know about new features. We release a couple every week. Hopefully, we keep them thinking that this product keeps growing and getting better.

Advice on increasing conversions and reducing churn

To increase conversions, send emails to your customers based on what they’ve done in your app. Most email marketing, including Drip, has tagging built in.

Reach out to your most engaged people and confirm they are going to convert. Send a broadcast to your lower engaged people and ask why they’re not using it.

The lowest hanging fruit for reducing churn is to help customers get more value out of the product.

The first time a customer creates a project or a campaign or whatever, throw an event into marketing automation and ping them over email, “Hey I saw you do X… Here’s a cool guide on what to do next…”

The optimal thing to do is to customize how far your customers have gotten into your onboarding flow… Regardless, emails work. They’re one of the biggest wins we’ve seen.

Whatever you do, definitely get emails going. You can get up 3-5 emails really quickly.


This is the first interview on our Things That Don’t Scale series. Sign up below to get updates as soon as we publish new ones.

What is Concierge Onboarding? Read about All Aboard!

Photo credit: @robwalling