The Startup Chat with Steli and Hiten
461: The Messy Middle
Oct 29, 2019
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In today’s episode of The Startup Chat, Steli and Hiten talk about the messy middle.

As your startup grows, new challenges arise. Processes and strategies that you used in the early stages are not the same pones you’ll use at the middle stages. Adapting to new changes is something you want to get right, as getting this wrong can have a negative effect on your startup.

In today’s episode, Steli and Hiten talk about how every company you work on now is uniquely different, why the middle is messy, what a messy middle looks like for a real company and much more. 

Time Stamped Show Notes:

00:00 About today’s topic.

00:35 Why this topic was chosen.

02:58 How every company you work on now is uniquely different.

03:40 Why the middle is messy.

04:42 How tech debt is one of the messiest things you can have.

05:00 What a messy middle looks like for a real company.

07:09 How marketing can be one of the messiest things about a company.

08:24 Steli’s experience with messy middles.

09:00 One of the biggest challenges about running a startup at the early stages.

10:10 Why things you did in the early days isn’t what you’ll use at the later stages.

3 Key Points:

It’s really crazy how whatever company you’re working on now is totally different from past ones.The reason its a messy middle is that what got you in the middle usually means you’ve created a mess.Tech debt is one of the messiest things you can have


Steli Efti: Hey everybody, this is Steli Efti.


Hiten Shah: And this is Hiten Shah.


Steli Efti: And today on The Startup Chat, we're going to talk about the messy middle. Or what I like to call it, the awkward teenage years of your business. So we've talked a ton about the super early stage days like how to come up with an idea, how to validate an idea, how to build an MVP, how to get your first customer, your first 10 customers, how to hire your first couple of team members. Like we've talked a ton about kind of the super early days as founders in your startup. And a lot of the topics that we discussed kind of touch all stages and phases of the business. But today I wanted to talk to you about what the most awkward time, and probably the the largest phase, or maybe not the largest, but it'd be a kind of significant phase, which is the phase in your company where your business is up and running. You have customers, you have customer growth, you have a bunch of team members. And kind of you're not in the hyper early pre product market fit. We don't know what we're doing. We don't know who's our buyer. We don't know if we're going to ever generate any money or how to market and sell and grow this thing. You're not in those early days. You've passed through that stage of your startup, but you're not quite yet at a place where you just add hyper scale and hyper growth or where you're now a super mature, super stable business. You're kind of in the awkward middle phase. And I wanted to chat with you a little bit about kind of, we've both gone through these phases with multiple businesses. What do founders need to know about the messy middle? How do they need to prepare for it? What mistakes to avoid? I thought it'd be fun for us to unpack kind of the most awkward phase of your business basically.


Hiten Shah: Yeah, so Scott Belsky and his now I think Chief Product Officer at Adobe, he wrote a whole book with the title, The Messy Middle. So we should definitely give him a shout out. Bumped into him somewhere the other day in the morning and I didn't recognize him. He's looking a little different these days. Looking good though. And so yeah, wanted to shout out. Great book, you should read it. That being said, we've got our own thoughts on this, so we should share our thoughts that have probably very little to do with what's in the book,

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