Fueling Startup Success With Collin Stewart

Collin Stewart is the Founder and CEO of Predictable Revenue, a sales outsourcing company that helps B2B businesses build repeatable, scalable sales development teams. Under his leadership, Predictable Revenue has become a recognized leader in sales consulting, delivering over 10,000 booked meetings and scaling outbound sales for more than 55 companies. Recognized for his data-driven, practical approach to solving sales challenges, Collin also hosts the Predictable Revenue podcast, which boasts over 400 episodes.

Here’s a glimpse of what you’ll learn:

• [3:39] Collin Stewart explains how Predictable Revenue began with cold emails
• [5:19] Case study with Brian Neman of Sanguine Bio on scaling outbound sales
• [7:37] How Predictable Revenue expanded beyond email prospecting to SDR teams
• [8:20] Why Collin recommends the tool Clay for hyper-targeted campaigns
• [10:56] Best practices for improving cold email deliverability
• [12:50] Common mistakes founders make with messaging
• [17:42] Why premature scaling is the leading cause of startup failure
• [23:08] Key questions Collin asks in his customer development process
• [27:09] How building a product without validated demand can waste years
• [39:12] Lessons from Uber Eats and Collin’s favorite books and podcasts

In this episode…

Rushing to scale before confirming real market demand is a common startup trap. Founders may hire sales leaders too soon, invest heavily in marketing, and burn through cash without a proven customer pull. How can entrepreneurs mitigate this risk and develop a sales process that truly meets customer needs?

Collin Stewart, an expert in outbound sales and customer development, learned this lesson firsthand. In his early ventures, he invested heavily in building tools without confirming that buyers cared, which cost him years of effort. Over time, Collin discovered that the key was starting with customer development interviews, asking the right questions, and carefully transitioning from learning conversations into sales. He now advises founders to validate product-market fit themselves before handing sales off, to avoid what he calls “founder suicide.”

In this episode of the Inspired Insider Podcast, Dr. Jeremy Weisz interviews Collin Stewart, Founder and CEO of Predictable Revenue, about bridging the gap between customer development and sales. Collin shares why premature scaling is a startup killer, his framework for running effective customer interviews, and lessons from working with companies like Uber. He also discusses best practices for cold email deliverability, targeting strategies, and his favorite tools for modern sales teams.

Resources mentioned in this episode:

• Collin Stewart on LinkedIn
• Predictable Revenue
• The Predictable Revenue Podcast
• The Terrifying Art of Finding Customers: A Sleep-Deprived Founder’s Guide to Revenue by Collin Stewart
• Brian Neman on LinkedIn
• Sanguine
• Clay
• The Mom Test: How to talk to customers & learn if your business is a good idea when everyone is lying to you by Rob Fitzpatrick 
• The Startup Owner’s Manual: The Step-By-Step Guide for Building a Great Company by Steve Blank and Bob Dorf
• The Four Steps to the Epiphany: Successful Strategies for Products that Win by Steve Blank
• Lean Customer Development: Building Products Your Customers Will Buy by Cindy Alvarez
• The Lean Product Playbook: How to Innovate with Minimum Viable Products and Rapid Customer Feedback by Dan Olsen
• Good Strategy Bad Strategy: The Difference and Why It Matters by Richard Rumelt
• The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture by Scott Belsky
• Stop Asking Questions: How to Lead High-Impact Interviews and Learn Anything from Anyone by Andrew Warner
• “How Zendesk’s Jaimie Buss trains and transforms leaders” on The Predictable Revenue Podcast
• “The Truth About Validating Your Startup Idea with Mase Issa” on The Predictable Revenue Podcast 
• “The Framework For Creating a Product – And a Brand-New Category” on The Predictable Revenue Podcast

Related episodes:

• “Automation Solutions with Wade Foster Founder of Zapier” on the Inspired Insider Podcast
• “Pipedrive: Brain Surgery, Married, & Moved Company from Estonia to U.S. All at Once – with Urmas Purde [Inspiration]” on the Inspired Insider Podcast
• “The Impact of Automation and Email Marketing with Tom Kulzer Founder of AWeber” on the Inspired Insider Podcast
• “[SaaS Series] Tips To Thrive in the SaaS Space With Sujan Patel” on the Inspired Insider Podcast
• “How To Build Deeper Relationships (And How To Handle a Shoved Fact) With Andrew Warner of Mixergy” on the Inspired Insider Podcast

Quotable moments:

• “The number one way companies commit suicide is premature scaling, investing in growth before finding a strong product-market fit.”
• “You should sell to those people you do your customer development research with because you can’t call it customer development if none of them give you money.”
• “If you’re a founder, you’re the best salesperson your company has ever seen, even if you don’t think you’re good at sales.”
• “Product market fit isn’t a binary switch; it’s a spectrum of weak to strong, evolving as you learn and adapt.”
• “Only the founder can prove the process to close a new customer; nobody understands the problem space better than you.”

Action Steps:

1. Improve targeting accuracy: Focus on a specific audience to reduce wasted resources and increase engagement.
2. Enhance email deliverability: Use multiple accounts and maintain a low, steady volume to avoid spam filters and reach recipients.
3. Conduct customer development interviews: Hold exploratory conversations to uncover real pain points and validate product-market fit.
4. Leverage referrals for validation: Track interview referrals to confirm true demand and focus on solving high-priority problems.
5. Prioritize tasks by value: Retain control of high-value sales activities while delegating lower-level tasks to optimize growth.

Episode Transcript

Intro: 00:15

You are listening to Inspired Insider with your host, Dr. Jeremy Weisz.

Dr. Jeremy Weisz: 00:22

Dr. Jeremy Weisz here, Founder of InspiredInsider.com, where I talk with inspirational entrepreneurs and leaders. Today is no different. I have Collin Stewart. You can check him out at PredictableRevenue.com. Collin, before I formally introduce you, I always like to point out other episodes of the podcast people should check out. We’re going to mention some of your favorite show, favorite episodes on your podcast too.

But I love some of your episodes on software and tools, so some of the ones I had on the co-founder of Zapier was a really good one, Wade Foster. I had one of the co-founders of Pipedrive on and I think at the time, Collin, they had like 10,000 customers. I think now they have over 100,000, so they’ve grown quite a bit. The founder of AWeber, I had on. I don’t know. When I think of you, I think of software and tools. So I’m thinking of those. But there’s many more. Mailshake was an interesting one. I think they like 70,000, over 70,000 users.

And so, you know, we’re going to get into Collin. Collin knows a lot and uses a lot of different software and tools, especially when it comes to sales and outreach. So we’re going to talk about his recommendations as well. But check those episodes out on InspiredInsider.com.

This episode is brought to you by Rise25. At Rise25, we help businesses give to and connect to their dream relationships and partnerships. How do we do that? We do that in two ways. One, we help companies launch and run a podcast. Right? We are an easy button for a company to do that. We do the accountability, the strategy and the full execution. So Collin, we call ourselves the magic elves that run in the background and make it look easy so the host can create amazing content, create amazing relationships, most importantly run their business.

The second way is we do corporate gifting. You know, so we will do automatic gifting for people’s clients. They just send us the list. We set up a sequence. We do it for our clients and our partners and they may get gifts from us. I’m not going to give away how often we send them, but multiple times a year for years to come, just as like a nice touch point to give to them. And we set it on autopilot for companies so they can just hand it off to us. And we do everything else.

So, you know, for me, Collin, we’ve known each other for a long time here. The number one thing in my life is relationships. I’m always looking at ways on how I can give to my best relationships, and I found no better way with those two things, with podcasting and sending nice appreciation gifts over the past decade. So if you thought about either of those things, you could check out Rise25.com or email us at [email protected].

I am super excited to introduce Collin Stewart, three time founder, currently founder and CEO of Predictable Revenue. You can check them out at PredictableRevenue.com where they’ve built sales development teams for companies like Uber, Top Tale, Vox and many, many more. He wrote the book called The Terrifying Art of Finding Customers, where he breaks down how to bridge the gap between customer development and sales. So he works with founders on finding and strengthening their product market fit. And Collin, thanks for joining me.

Collin Stewart: 03:27

Jeremy, thanks for having me on the show. That’s quite the intro.

Dr. Jeremy Weisz: 03:30

Just start off and I’m going to share your website, Predictable Revenue. Talk about what you and the company do.

Collin Stewart: 03:39

Well, I mean I’ll give you the short version because the long story is pretty long and we don’t have three hours to record here. But the short version is we started off, I bootstrapped Predictable Revenue and started off as a company that basically. I mean, it was really just me helping my friends send cold emails. It’s something I figured out how to do 13 years ago while I was trying to start a CRM company, and I just started doing it because it brought revenue and I didn’t want to, I didn’t want to raise money, didn’t think we needed to raise money. Conversation for a different day. What we do now is we’re still pretty strong on the outbound side and the sales development side. But it’s more working with founders to help find their first customers, helping founders stand up, that first outbound team, or the first demand gen channel. And it’s typically outbound, typically outbound email.

And we do a lot. I think my favorite work right now is just working with founders on whether you’re using outbound to book customer development meetings or you’re using it to kind of scale up your first customers, we kind of help. I love helping founders kind of strengthen the product market fit, you know, book meetings or interviews so they can, their customer development interviews so they can learn more and then transition those conversations, teach them how to transition those conversations from learning conversations into revenue conversations.

Dr. Jeremy Weisz: 04:58

Yeah. So you could see I mean you have sales consulting. You have outsourced sales and founder coaching. I want to break those down a little bit, but maybe we’ll talk about it in the form of an example, so people can kind of get some knowledge on how it works and also how it works for someone else. Maybe talk about Brian Neman for a second.

Collin Stewart: 05:19

Brian is a founder I got a chance to work with. So Brian is our biggest fan. If you ever meet Brian or talk to Brian, he’s the founder of Sanguine Bio and I think in Sanguine Biosciences. We’ve yeah, I’ve done work with his wife. He just introduced me to his brother in law. Like they both have their own companies. But what I did with Brian was basically what I did, I described in the intro.

Dr. Jeremy Weisz: 05:41

Where was he at when you, he was solo at the time?

Collin Stewart: 05:48

Maybe he had a co-founder, but it was Brian hustling and selling and struggling with the pipeline. And he had read and reached out to us. And I got the first call with him and basically helped him build a system that just booked meetings for him. And so we built a –

Dr. Jeremy Weisz: 06:10

Is this the right place? Is it Sanguine?

Collin Stewart: 06:11

Yeah. SanguineBio.com

Dr. Jeremy Weisz: 06:12

Okay.

Collin Stewart: 06:13

You got. Yeah. They’re super, super cool. And I initially told them, like, I don’t think it’s going to work. Like, I don’t think we’ll be able to find the right folks and I don’t know why.

Dr. Jeremy Weisz: 06:20

Why did you think that?

Collin Stewart: 06:20

It seemed a little bit outside of our sweet spot in terms of who he wanted to reach. So it’s basically like from what I remember is matching patients to studies is what he was helping do in the, like the bioscience studies field. And I was like, I don’t think, I hadn’t done that before. And I’m generally pretty candid with people coming in ahead of time. I’m like, if I’ve done it, I’m like, yeah, I’m bullish. I can do this. And if it’s if there’s some uncertainty, I’m pretty candid about, like, hey, I don’t think it’s going to work. And every time I say it’s not, I don’t think it’s going to work like it worked extremely well for Brian. And he’s been our biggest fan ever since.

But basically, we built a system initially that was sending emails from his email account and booking meetings for him, and then he got so busy with that he had to hire some salespeople. So we helped him with that and then helped them build the systems to have his salespeople have the emails going out on behalf of the salespeople. Our team was booking meetings for his salespeople. We kind of grew alongside him as his company grew.

Dr. Jeremy Weisz: 07:23

So it sounds like, was he doing all three of these then? Like you start off, it sounds like maybe the sales, consulting and coaching is embedded into if you’re helping them. You know, as far as the outsource SDR piece.

Collin Stewart: 07:37

Our solutions have evolved over time. But yeah, it started off with like we were just doing email only prospecting at the time. And it’s been interesting, the kind of arc of Predictable Revenue. We started off 100% email only in 2018. We saw that email deliverability was kind of taking a hit. And we’re like the old way of doing things wasn’t working anymore. And so we brought in SDRs. And now what we’re seeing is that email is actually there’s a bit of a resurgence. And it comes down to the, you’ve heard me rant and ramble about Clay, so I won’t do that. You can maybe link it in the show notes.

Dr. Jeremy Weisz: 08:11

Yeah you can, you can talk a little bit about it just because I’ve heard it. Other people haven’t. So feel free to share any tools, software that you are bullish on.

Collin Stewart: 08:20

It’s basically a spreadsheet for sales nerds. And you can do some like really crazy things in there, like designing micro campaigns for left handed founders that play guitar. I mean, that’s a pretty silly example, but you can almost, almost get there with Clay. If you open it up, you’re going to look at it and go like it just looks like Google Sheets, but worse because there’s nothing in it. And so if you’re going to check it out, email me and I’ll send you a couple of resources or just look in their knowledge library like they got some crazy stuff in there.

But I think with Clay, Clay and tools like it, there’s been a resurgence in cold email because you’re not just limited to the standard filters in your data source anymore. It’s not just size of company, size of employees, you know, job title. You can get so much deeper than that. And that was the piece that really opened our eyes. And we’re back right into cold email, cold LinkedIn, but really small, really targeted campaigns.

Dr. Jeremy Weisz: 09:16

Talk about the tools for a second, right? You know, because you mentioned obviously the services have evolved, right. So it started off as email. You know, you do consulting, founder coaching and then outsource SDR. But you do calls as well. So what are some of the tools that you like to utilize from a productivity and efficiency standpoint?

Collin Stewart: 09:40

From an efficiency standpoint this is another one. So first up, if you have the best message in the world and you send your team after the wrong people, it doesn’t matter how good their scripts are, their emails are their follow up, their execution, their everything. If you’re trying to sell, you know, Rise25 podcasting and you send them after farmers in Nebraska, like, I don’t care how good your SDR team is, you’re probably not going to get the greatest response, because I just don’t think podcasting is in the farming business business model, right? It’s just not something that would make sense. And so it’s not relevant to them. It’s not going to get a great response.

And so the number one thing that’s changed in the last little bit has been the targeting. I can when you build a great list with Clay, you can get really targeted and say, okay, it’s these specific folks for this specific reason. And we know they’re more likely to be ready to reply because of these 3 to 4 things. And we’ll build these like account qualification models that filter and sort people into the right buckets. So that’s kind of step one. Step two email deliverability. There’s a bunch of geeky stuff that’s changed lately. Email me or I can send something to Jeremy if you want, like a cold email deliverability guide.

Dr. Jeremy Weisz: 10:52

What are a few things on that? Maybe 1 or 2 things on that end?

Collin Stewart: 10:56

I think just, you know, more email accounts and domains than you think are necessary and a low volume. And make sure you’re ramping your email. You’re warming up the mailboxes and keeping them to below 30 a day. And that’s really what you want to do is show Google that you’re a consistent sender. You don’t want to have big spikes, because I think the stat I heard of like ten years ago was like 90%. This is ten years ago, and 95% of Gmail accounts were created for the purpose of spam. And the reason is there’s no history. And so every Gmail account that’s created starts life with pretty good deliverability. But then after it sends a few emails, they see, oh, wow, it’s actually, these are garbage. This is spam. But you don’t know until you’ve seen a few emails.

And so Google uses this quarantining system. It basically means that every new Google or Gmail or Google Apps account gets really good deliverability for the first ten messages, so spammers know that and they send. They set up what’s called snowshoe spamming, and they set up 10,000 Gmail accounts and they send ten emails from each one. And so what you want to do is avoid looking like that and have us, you know, do the math on like what’s acceptable per inbox from a Google perspective and then just send a consistent volume. And make sure that the most important thing is that your messages are relevant.

Because the most important thing for Google is that people open reply, you know, forward click on your emails, right? The only thing they care about is engagement. And if you’re not engaging with those emails, then they start to care about a lot of other things.

Dr. Jeremy Weisz: 12:31

So we have the right audience targeting. We have email deliverability and we have message relevance. What are some mistakes people make under that category?

Collin Stewart: 12:44

Under relevance?

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