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Rogue Startups

RogueStartups
Rogue Startups
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  • RS346: What 11 Years in SaaS Really Looks Like
    In this episode of the podcast, Craig sits down with longtime entrepreneur Colin Bartlett, cofounder of StatusGator, to explore what it really takes to build, and sustain, a SaaS business over the long haul. With more than a decade at the helm of a company that helps users monitor service outages, Colin shares hard-won insights from 12 years of entrepreneurship and 11 years of running StatusGator. The conversation dives into how founders’ perspectives evolve, especially in today’s turbulent tech landscape, and how to stay grounded and successful through all of that craziness. Highlights from Craig and Colin’s conversation: How Colin and StatusGator did when Google Cloud went down for a few hours The factors that can determine whether or not free trials can work for your business The difference between the company in the beginning versus 10+ years down the road How their businesses fit into the current markets (alongside AI and other tech advances) Appreciation and respect for the businesses in such uncertainty Plans, trajectories, and what the future holds for them Views on profit in the SaaS industry Their team structures and how to hire and maintain a team in the AI era Staying fresh in the market after you’ve been in the business for a while The benefits of having a cofounder SOC 2 (System and Organization Controls 2) compliance and privacy standards How many hours does your team have to work to be a value to your company?   Resources and Links from This Episode Colin Bartlett on LinkedIn: https://www.linkedin.com/in/colinabartlett/ StatusGator: https://statusgator.com/ If you feel like Rogue Startups 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. Do you have any comments, questions, or topic ideas for future episodes? Feel free to reach out to me: Twitter: @TheCraigHewitt LinkedIn: Craig Hewitt Email: [email protected]   Chapters (00:00:00) - Talking Startup With Colin Bartlett(00:01:51) - Flare on the Internet Outage(00:03:48) - How Do You Capture Leads From Free Signups?(00:09:18) - How Long Can You Keep Working On Your Startup?(00:14:42) - How Do You Think Your SaaS Business Should Be Profitable(00:16:53) - What Your Team Looks Like on SaaS(00:19:12) - How We Run a WordPress Team(00:21:34) - How to Hire a Team in the AI Era(00:25:46) - Top Executives: How AI Will Affect the Business in 2(00:31:20) - Podcaster on An Economic Dip(00:32:17) - How Do We Stay Fresh After 11 Years?(00:37:22) - If You Had to Pick A Boss, What Would You Do?(00:38:39) - Cisco on SOC2 Compliance(00:42:30) - How much Time Should Your Team Work?(00:46:48) - How To Get Things Done As A CEO
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  • RS345: The State Of Search 2025
    - LLMs.txt article: https://www.quoleady.com/llm-txt-files/ - Craig's YouTube channel: https://youtube.com/@thecraighewitt   Chapters (00:00:01) - Rogue Startups: The Startup Podcast(00:00:07) - Content Marketing: Multimodal(00:03:37) - Is Content Necessary for Your Business?(00:06:23) - How to get a crawler to crawl your website for SEO(00:13:58) - Marketing Decoded: Content and Search(00:17:14) - Want to hear more of my ranting on AI?
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  • RS344: 12 Years to Overnight Success with Amar Ghose
    What does it really take to lead a company for over a decade—and still be growing? In this episode, Craig chats with Amar Ghose, founder and longtime CEO of ZenMaid, about the challenges, lessons, and evolution that come from running a SaaS company for 12 years. From market leadership and internal conflict to personal growth and productivity, Amar shares candid insights into the realities of long-term entrepreneurship. Whether you're scaling a startup, feeling stagnant in your leadership role, or just wondering if AI is going to eat your SaaS lunch, this conversation delivers.   Highlights from Craig and Amar's conversation: Transitioning from following trends to becoming a category leader Navigating internal disagreements and managing tough decisions Running a "benevolent dictatorship"—and why that sometimes works How to deal with boredom, complacency, and staying sharp as a CEO The productivity paradox: what being "productive" means at the top Entertainment vs. distraction: protecting your focus How coaching reveals your blind spots (and helps you evolve) Staying out of cruise control—how to keep leveling up, year after year Is AI a threat to SaaS companies, or a tool for growth? Takeaways and Vision Longevity in SaaS isn’t about coasting. It’s about evolving. Amar Ghose proves that staying in the game for 12+ years means embracing discomfort, sharpening your focus, and leading with intention. Whether you're one year in or a decade deep, this episode is a reminder: real leadership isn’t about avoiding boredom, it’s about leveling up through it. Resources and Links from This Episode ZenMaid – Amar’s SaaS for maid service businesses Follow Amar on LinkedIn Rogue Startups Podcast Archive Connect with Craig on Twitter/X: @TheCraigHewitt If you feel like Rogue Startups 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.  Do you have any comments, questions, or topic ideas for future episodes? Feel free to reach out to me: Chapters (00:00:00) - How to Build a 12-Year-Old SaaS Company(00:01:15) - Squarespace CEO on How Far Along the Business Is(00:03:39) - How We Went From Fast Follower to Industry Leader(00:08:35) - Jeff Bezos on Decisions Made by the Team(00:13:52) - Zenmaid's CEO on Never Enough(00:18:10) - How to Get More Out of a Manager(00:19:30) - Craig on His Side Businesses(00:25:49) - Kastos on What Would He Tell You?(00:28:03) - How Do You Continue to Evolve As a Founder?(00:33:16) - Brain tumor patient on work life balance(00:39:46) - Jordan G. on AI and the Economy(00:44:55) - Brands and the AI revolution(00:46:33) - Amar Ghosh on Connecting With People
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  • A Caffeine Infused Diatribe
    Hello, remember me?  Sorry that it's been 6 weeks, but I'm back. In this episode I talk through what I've been up to recently, what's going on with Castos, with myself personally, and things I'm learning growing the business.  Towards the end, I share the lessons I learned from a recent 2-day Scaling Workshop with Alex and Leila Hormozi.  The event was great, and really reframed how I am thinking about the business, and about being a business owner.   My YouTube channel: https://youtube.com/@thecraighewitt - for sales, marketing, and founder-focused content like this. Chapters (00:00:00) - What's Up With Me(00:00:38) - Top Creators: AI and How to Use It(00:06:21) - How We're Going to Implement Hybrid Podcasting(00:10:36) - How I'm Using AI on My Personal Channel(00:14:27) - Writing Content Is Dead on Social Media(00:17:43) - A Retrospective on The Kastos Scaling Workshop(00:18:43) - Interview(00:19:14) - The Warren Buffett Lecture(00:21:19) - Six Metrics That Make Up My Business(00:23:17) - Top Executives: Paid Acquisition(00:24:39) - Keeping Person in the Business(00:25:42) - What is the Key Customer Risk?(00:27:16) - Key Market Risks(00:29:15) - Sales Funnels and How to Manage Them(00:30:37) - How to Get More Out of Your Work Life(00:31:40) - How to Scale a Startup: The Castos(00:34:01) - The Four R's for Job Description(00:35:04) - How To Get Feedback From Your Sales System & Culture(00:37:12) - What They Look For In Their CRM Hiring(00:38:54) - Sales and Marketing: The Middle of the Revenue Cycle(00:42:21) - Castos: How to Make Paid Acquisition Work(00:45:28) - The Time Evaluation Workshop
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  • RS342: SaaS Survival Mode - AI, Niches & Navigating Chaos
    In this episode of Rogue Startups, Craig chats with Jesse Hanley, marketer, self-taught developer, and founder of Bento, a powerful email marketing platform for modern teams. With today’s economy in flux and global events adding more pressure, Craig and Jesse dive into what it really means to run and grow a SaaS business in 2025. They explore how entrepreneurs can protect their businesses and families in turbulent times, why niching down is more important than ever (but only for some), and how AI is transforming both Bento and Craig’s own company, Castos. From global living experiences to making tough decisions about free tiers, this episode is packed with honest insights, practical advice, and a few spicy takes on the future of SaaS. Highlights from Craig and Jesse’s conversation: Living and working in Japan, France, Australia, and the US: cultural and business differences Bento’s vision and how they are navigating economic uncertainty Knowing when to bring in experts (and when to trust your gut) How Bento is integrating AI—and how it’s driving real results for users Behind the scenes at Castos: using AI to boost productivity and creativity Are free plans a growth hack or a trap for SaaS companies? Marketing smarter: finding your ideal customers in a crowded market To niche or not to niche? What to do if your product is a Swiss Army knife If you’re a SaaS founder, bootstrapped entrepreneur, or just love behind-the-scenes looks at real businesses navigating real challenges, this episode is for you. Resources and Links from This Episode Jesse Hanley on Twitter/X: https://x.com/jessethanley  Bento: https://bentonow.com/  If you feel like Rogue Startups 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.  Do you have any comments, questions, or topic ideas for future episodes? Feel free to reach out to me: Twitter: @TheCraigHewitt LinkedIn: Chapters (00:00:00) - Interview + Co-Host Chat(00:02:34) - Visit Annecy, France(00:02:51) - Living in France as an American(00:04:39) - Trump on Trade Wars and AI(00:05:04) - Bento CEO on Working With Customers(00:07:41) - What's the rest of the team like?(00:11:02) - How to Hire an AI-Inspired Team(00:16:46) - Bento's CEO on How Long Will He Run the Business?(00:18:55) - Bento CEO on Cash Exclusion(00:23:53) - WSJD: Business Cycle, Uncertain Future(00:27:15) - Have We Should Offer a Free tier?(00:33:03) - Bento vs. Mailchimp: How To Reach Out to(00:38:41) - Bento on Being a Utility Tool(00:40:24) - Bento on Collaboration and Its Impact(00:43:52) - Community and the AI of Business
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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.
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