
Rogue Startups
On Rogue Startups we share the journey of startup founders as they're growing their businesses. We feature experts in the fields of sales, marketing, and product development to hear how they're growth hacking their productized services and SaaS products. If you're on the journey of an entrepreneur then tune and hear how we're tackling some of the same obstacles you may be facing, and how we're winning in the game of business. Listeners of Startups for the Rest of Us, My First Million, Mixergy, and Bootstrapped Web will love checking out our show.
Latest episodes

Mar 27, 2024 • 41min
RS305: Validating SaaS In An Enormous Market w/ Christopher Gimmer
Is there such a thing as the perfect SaaS business? How are you creating your opportunities? Are you focusing on your end goal for your business? Today, Craig is joined by Christopher Gimmer from Snappa and Good Metrics. Chris talks about his path, which led him to founding multiple businesses and a successful exit. He dives into his decision-making process and how he finds his next big opportunity. As entrepreneurs who have 100% bootstrapped their businesses, Craig and Chris talk about their processes, successes, and lessons they have learned on their journeys.
It can be hard to realize, narrow down, and make big-picture decisions for your company, especially if you’ve built it yourself. Yes, it is your baby, but it’s important to realize when to let go and when to grasp new opportunities.
Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!
Highlights:
Learning about best practice business models from previous endeavors
Expansion revenue vs low churn
The importance of keeping focused on business goals. Acquisition? Expansion?
How Chris finds, makes, and determines new opportunities
Pricing and business models
How to be business-critical
Naming: when to bite the bullet
The status of Good Metrics
Marketing and differentiating yourself from your competition
Horizontal vs Vertical SaaS businesses
Resources:
Find Chris on Twitter/X
Christopher Gimmer
Nathan Berry’s article, “Direct Sales for Bootstrapped SaaS Startups: from $1,300 to $725,000 MRR”
Castos
Founder Insights

Mar 20, 2024 • 46min
RS304: What Is Google Doing?! (w/ Spencer Haws)
The world of SEO is changing at a rapid pace because of AI. How can we keep up? Can you still find, generate, and publish unique content online? The answer is yes. Google says that around 20% of online searches every day are ones they’ve never seen before. Here to talk about all that is SEO and keyword guru, Spencer Haws.
In this episode of the Rogue Startups Podcast, Spencer and Craig both talk about how they use AI and how human writers can work with AI-generated content. Spencer also gives his crystal ball prediction of what SEO will look like in the next five years. They also chat about where the platform of podcasting fits in the content world, face-to-face conferences and masterminds, and the reasons to stay with a business after receiving buyout offers.
Spencer grew up in Mesa, Arizona, and moved to Richland, Washington. Because of the influence of his entrepreneur father and because he grew up during the dot com boom (and bust), he started dabbling in website creation in 2005. Since then, he has learned how search engine optimization works and how to best build and grow niche websites. The best way to contact Spencer with any questions or comments is here.
Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!
Highlights:
What is Link Whisperer and how will it help you
Is Rank Logic good for larger or smaller websites?
The best ways to use AI for content creation
Using AI for Listicles
SGE (Search Generative Experience) and SEO
Content development and marketing
Separating your business from your life
How Spencer keeps up with the evolution of the industry
Books versus podcasts
The importance of conferences, masterminds, and business groups
To exit or not to exit, that is the question
Resources:
Reach out to Spencer
Connect with Spencer on Twitter/X
Rank Logic
Link Whisper
Niche Pursuits
Castos
Founder Insights

Mar 14, 2024 • 14min
RS303: After The Desert
In this solo episode, Craig talks through a recent mindset shift in the business.
https://youtu.be/vG0YKhAdPl0
Going from Zero to One you need to put out so many fires, and do so many things, and then in the growth phase you’re constantly trying new approaches, channels, messages, and levers. Here in the post-growth, calm phase, Craig’s found it a bit different to balance the Certainty and Uncertainty of running the business.
Craig’s also offering one-on-one founder coaching to SaaS founders looking to get from 0 to $3M ARR – head over to craighewitt.me/coaching to find out more and schedule a free consultation.

Feb 19, 2024 • 54min
RS302: Beyond Content Marketing with Doug Cunnington
Doug Cunnington is an affiliate marketing, SEO, AI, and content marketing expert. Today, Craig and Doug chat about their experiences as founders and with web content, in hopes that they can learn from each other and pass along some tidbits of info to listeners.
AI-generated content is everywhere these days. The content marketing industry is split down the middle: they either embrace it or are pushing back. Is it worth it? Craig and Doug deep dive into their opinions on AI content, how they use it, and what the future of content marketing looks like. They talk about their cadence on YouTube and various other platforms. They also chat about exiting, retirement, and their paths now that they’re getting older.
Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!
Highlights:
Doug’s journey to content marketing
Position yourself so you don’t have to react immediately
The constantly changing industry of content
The value of a content marketing strategy
AI-generated content
Scripting for YouTube: shorter, tighter videos
Entrepreneurship and SaaS as you get older
Feeding the YouTube algorithm what it wants
Content strategy differences between YouTube and podcasts
Resources:
Doug’s YouTube Channel
Castos
Founder Insights

Jan 31, 2024 • 48min
RS301: Why Brands Grow with Marc Thomas
One of the biggest lessons Marc Thomas learned about creating engaging content was the importance of bringing in bits of his personality. Today, Craig talks with Marc Thomas about how he has made a name for himself in the world of content and brand growth. Marc emphasizes what some of us forgot: B2B content has a purpose and we have to know what that purpose is. They also talk about the effectiveness of marketing “best practices,” the importance of transparency, Podia’s biggest marketing push and how it worked, and competitor landing pages.
Marc Thomas is the Senior Growth Marketer at Podia. Since 2014, Podia has been committed to building the most creator-friendly tools to help their customers sell online courses, digital downloads, membership subscriptions, and more to their audience.
Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!
Highlights:
The justification for B2B content: it doesn’t have to be boring and it has a purpose
Connecting your customers to a business outcome
How Podia created engaging, viral B2B content
Lessons from How Brands Grow by Byron Sharp
Vertical versus horizontal SaaS
Do marketing best practices really work?
Generosity and transparency
Competitor landing pages are insurance policies for your buyers
Continuing to learn and refine your craft
Balancing personal growth and playbooks
Failure is relative; people are adaptable
Resources:
Marc Thomas, LinkedIn
“How Brands Grow: What Marketers Don’t Know” by Byron Sharp
Castos
Founder Insights

Jan 19, 2024 • 23min
RS300: What’s Killing Google, and Exiting The Startup Phase
It’s the 300th episode of Rogue Startups, and it’s all about personal updates and professional improvements. Craig talks about where Rogue Startups started and what the future holds for this podcast and podcasting in general. What mediums will everyone gravitate toward this year? Who will win in this cage match between Google, YouTube, AI, SEO, and social media?
Craig also talks about where he wants to spend his time and energy in 2024. He has an ambitious but achievable goal of creating and publishing 200 videos on YouTube this year. Not to mention, he dives into this theory on personal engagement and personal content and how those things will change soon as well. Will they be more or less important?
Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!
Highlights:
Evolving in the podcast industry
The difference between podcasting and YouTube
YouTube versus Google
What is the medium of the future?
AI trends and what that means for writers
Personal engagement and personal content
Diversifying beyond SEO content
The goal is optionality
Growth from the awkward teenage years to a mature adult
Building the right system and getting the right team
Resources:
Castos
Founder Insights

Jan 12, 2024 • 50min
RS299: YouTube Scripting Done Right with George Blackman
George Blackman joins Craig in this installment of the Rogue Startups YouTube series. They chat about scripting episodes and what you can do to prepare yourself for making successful videos. George has had years of experience working with successful YouTubers who have had millions of views on their videos, in part because of George’s scripts.
George and Craig also discuss why scripting is important, how to use a teleprompter, and the pros and cons of riffing versus being intentional and planning content. On the topic of AI, they focus on how he utilizes AI for title creation. One example of a prompt being:
“I am writing a video based on a topic and a “grand payoff” that I’ll provide below. Based on these two components, what emotional transformation will viewers have experienced by the end? (Related to the Grand Payoff)
Question/Topic: [insert here]
Grand Payoff: Viewers will understand XYZ.”
George is a consulting YouTube scriptwriter based just outside London. He has written scripts for creators like Ali Abdaal, Noah Kagan, Creator Booth, and Mike Shake. His new course (”YouTube Scriptwriter’s Playbook” Course) focuses on systemizing the process of scriptwriting to maximize retention. It starts on January 12th. Join in at a discount by using the code: launch10.
Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!
Highlights:
Improvising versus planned content
Find the key “punchy” moments from your notes
Sewing together mini-payoffs
Set-up, tension, and resolution
Start listicles with a punchy start, in the middle, and at the end
Thread in story elements and relevant personal anecdotes
How scripting saves time
Beginner teleprompter tips
George’s process for creating great videos:
Retention checklist: Information, progression, regression, and emotion
Creating and planning payoffs and tension
Repetition. Are you repeating information?
Clarity: conversational scripts that sound like yourself
AI and scriptwriting
YouTube versus Twitter/X
Tips for educational and informative videos
Analyzing your videos to create better content
Resources:
George’s website
”YouTube Scriptwriter’s Playbook” Course Discount Code: launch10
Connect with George on Twitter/X
Castos
Founder Insights

Dec 25, 2023 • 43min
RS298: 3 Steps To Move Your YouTube Channel To The Next Level with Trent Haire
Trent Haire drops some serious knowledge as he chats with Craig today about the three things that you can do to move your YouTube channel to the next level. Trent has years of experience and has worked with some major YouTubers by helping them go from little to no viewer and subscribers to thousands and even millions. In addition to his tips, they also talk about how B2B YouTube strategies differ from other YouTube channels, the importance of providing value first, and how YouTube stacks up to other social media platforms with shorter content.
Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. And as always, if you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!
Highlights:
How to get over the hurdle and start making videos
Setting good expectations
Making progress and improving is the main goal
B2B strategies and how they differ from others
“Hiding your vegetables”
Top of Funnel content and conversion
YouTube versus LinkedIn versus Twitter/X
Providing value first
Discoverability and search versus suggested
Tracking the stats on your videos and updating the packaging
Long-form videos versus shorts
Three ways to bump your channel up to the next level
Resources:
Creator Campfire
Trent Haire on Twitter/X
Castos
Founder Insights

Dec 18, 2023 • 46min
RS297: YouTube Channel Teardown with Josh Howard
Today’s episode is all about YouTube SEO. Craig is joined by Josh Howard, YouTube expert. Josh shares his knowledge about how to rank your video #1, and how to be successful in constructing a dynamic script and structure for your channel and individual videos. He also shows this information in action by analyzing Castos’ YouTube page, as well as Ahrefs’ YouTube channel.
Josh Howard started his analytics journey with website SEO before transitioning fully to YouTube. He used his love of math, statistics (and spreadsheets) as a foundation for understanding how to succeed on YouTube. He helps his clients make better content, utilize YouTube in valuable ways, and understand the analytics behind their videos to maximize the performance of their channels.
Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. As always, if you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!
Highlights:
People don’t go to YouTube to buy things, they go for free information
Where SaaS companies should put their YouTube content
Targetting search trends and potential
YouTube, the middle of the funnel
One keyword, one article, one time
The balance of evergreen and timely content
Analyzing Castos’ YouTube channel
Constructing YouTube playlists well
Keeping long-form content relevant
Call to Action on YouTube videos
Resources:
Reach out to Josh on Twitter
Connect with Josh on LinkedIn
Check out Josh’s personal website
Castos
Founder Insights

Dec 11, 2023 • 48min
RS296: Creating Great YouTube Hooks with Jake Thomas [YouTube Series]
Today Craig chats with Jake Thomas from Creator Hooks about what SaaS owners and entrepreneurs can do to catch the eye of possible customers and viewers on YouTube. Jake started his journey to Creator Hooks when he landed his dream job as a marketing manager at a fishing company. There, he learned the most important thing about creating titles and content for YouTube: modeling other successful YouTube videos. In today’s episode, Jake talks about that process as well as the importance of authenticity, posting on different social media platforms, and how to position topics in a way that will draw people in.
Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. And as always, if you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!
Highlights:
Building your YouTube channel without being someone you’re not
How older companies can stay trending: Edu-tainment
Types of content SaaS companies should produce
Competing in a saturated niche
Where to post different types of content on social media
Quick and dirty research tips
Quality versus Quantity
Positioning topics in an interesting way to get people to click
Topic and frame
How Creator Hooks can help you
Curiosity, Fear, and Desire
Split-testing thumbnails
Resources:
Creator Hooks
Reach out to Jake on Twitter/X
Castos
Founder Insights