Rogue Startups – Détails, épisodes et analyse

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Rogue Startups

RogueStartups

Business & Entrepreneuriat

Technologie

Fréquence : 1 épisode/10j. Total Éps: 50

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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RS341: Microconf 2025 Recap

mercredi 26 mars 2025 • Durée 17:48

Craig recaps his biggest takeaways from MicroConf 2025, reflecting on lessons in positioning, lead generation, conference ROI, and the power of going all in on what’s working. From tactical marketing insights to personal reflections, this episode delivers both strategic clarity and founder fuel.

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RS340: Is AI Killing SaaS w/ Tim Schumacher

mercredi 19 mars 2025 • Durée 43:00

In this episode of Rogue Startups, Craig sits down with founder and entrepreneur Tim Schumacher to discuss his insights on AI, the future of SaaS, and what makes a company successful.

In 2001, Tim co-founded Sedo.com, the world's largest domain marketplace. Since selling the company, he’s been active as an Entrepreneur and/or Investor in various start-ups, such as Eyeo (makers of Adblock Plus), Ecosia, Hitfox, Aklamio, Miomente, PiwikPro, BasicThinking, Home, Zolar, Joblift, SaaS.group, and others.

Highlights from Craig and Tim’s conversation:

The future of SaaS keeps founders up at night
Using artificial intelligence to analyze feedback and company metrics for smarter decision-making
How to make your data, and your customers' data, available across multiple platforms and environments
What impact will AI and automation have on the economy and the future of work?
Why are some in the SaaS industry still hesitant to adopt AI, and what are their fears?
Key factors that drive business growth and longevity.
Product-Market Fit vs Founder-Market Fit: Understanding the difference and why both matter.
Starting a business at the intersection between climate tech and AI
Remote work vs in-office culture: How the workplace dynamic is evolving in the age of digital transformation.

Resources and Links Mention in This Episode:

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:

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RS339: AI Skeptic, or Believer

mercredi 5 mars 2025 • Durée 47:49

In today’s episode, Craig chats with Anthony Eden from DNSimple about how they use AI in their businesses and their personal lives. As early skeptics of AI, they do a deep dive into what made them change their minds, what AI does for them, and how it might actually be holding people back. Like the internet, AI is a powerful tool people can use to make their lives better.

They also chat about what it’s like to raise kids as entrepreneurs. Has their influence improved or hindered their children’s lives? Not to mention, how do they balance their work life and personal life and is AI helping them with that balance?

Anthony Eden is the creator and founder of DNSimple. He has been developing web applications since the early days of the web (1995) using Ruby, Erlang, Golang, and other languages. He used to publish a podcast called the Strong Businesses Podcast with Steven Bristol. He also published a mostly weekly podcast of progressive dance music over at theministerprime.com. He also produces tracks which can be found on SoundCloud.

Highlights from Craig and Anthony’s conversation:

What changed Anthony and Craig’s minds about AI
How to, as an entrepreneur, leverage AI without just “chasing the trend”
The personal and emotional impacts of running a business in this AI world
What AI will do for the future of business and SaaS
Training AI and what the “mistakes” teach you and your team
“I have to have a little bit of fear in everything I do [as a founder].”
Keeping customer data safe and secure
What data is AI using to aid you with your business?
“This kind of stuff is fantastic but, boy, does it make you lazy.”
As an entrepreneur, how do you talk to your kids about careers after college?
How is generative AI going to make our lives better?

Takeaways and Vision:

How do you take a non-native AI solution and adapt it to a solution for your customers, your team, and your business? As a founder and entrepreneur, how you use AI in your business is important. Not only do you have to pay attention to what information you are getting from AI, but how it is affecting your productivity overall.

RS338: Balancing Your Use of AI with Aaron Francis

Épisode 338

mercredi 26 février 2025 • Durée 52:12

Ever wonder what's happening behind the scenes when your dev team says they're "leveraging AI"? As a non-technical founder, you don't need to understand every line of code, but knowing how AI is actually being used in your business is becoming essential.

Today I'm sitting down with Aaron Francis, who pulls back the curtain on AI in development work. We'll explore the surprising differences between how veterans and newcomers in the field are using these tools, the common pitfalls teams fall into, and the unexpected ways AI is transforming how products get built. Whether you're trying to speak your developer's language or just want to ensure your company is using AI effectively, this conversation will give you the insights you need.

Highlights from this Episode:

Are junior developers utilizing AI too much?
Creating a balance between overusing AI and being a Luddite
How Aaron uses Claude for “discrete” tasks
Developers aren’t going away anytime soon
Balancing the use of AI without depending too much on it
Harnessing the power of AI for your business
AI tools are both calming and scary for founders
Aaron’s different uses for 01 Pro
What AI can do versus what AI should do and undeniably human tasks
Where to go to educate yourself about AI
The importance of testing and checking AI work

Resources and Links from this Episode:

Try Hard Studios: https://tryhardstudios.com/
Aaron Francis: https://x.com/aarondfrancis
Reforge: https://www.reforge.com/profiles/brian-balfour
SWYX: https://x.com/swyx
https://www.youtube.com/@JeffSu
https://www.youtube.com/@SkillLeapAI
https://www.youtube.com/@MATGpod
Email me: podcast@roguestartups.com
Find me on Twitter: https://twitter.com/TheCraigHewitt

RS337: Building AI Native SaaS w/ Jordan Gal

mercredi 5 février 2025 • Durée 48:06

Today, Craig chats with Jordan Gal from Rosie about starting a business centered solely on AI. While many of us use AI to help with our work tasks and streamline certain jobs, Jordan’s whole business is AI. They discuss how you and your customers can use AI, what it’s like to start a company right now, and what AI is doing to SaaS.

Rosie creates a new option for small businesses. Previously, the only way to handle phone calls during work hours was through voicemail or an answering service. Rosie offers a new option in that market: an AI can answer the phone for you and handle the tasks needed for these calls, whether it’s taking messages, sending messages out, or talking to clients.

Highlights from Craig and Jordan’s conversation:

Non-technical CEOs sympathize more with customers
- Jordan views his engineering company as customers see their product
- Because of this, he knows how Rosie helps businesses run better
Using AI to help the customer understand their data vs building a product that was not possible before AI
Create milestones for the team when creating a brand-new product
- Jordan tells his team to work as if they are onboarding 100 customers a day
Dealing with customers that have different knowledge bases of your type of product
- Remove marketing fluff to speak plainly to possible customers
- If you provide the customer with something they truly need and get value from, they will find ways to deal with those roadblocks
Conversion versus usage numbers: how to avoid churn
- Freemium and usage-based trials
What AI has done to SEO: people are led to video and YouTube
Software in the AI era
- Now is a good time to bootstrap; it is not a good time to raise money
Everything you do has to have leverage

Takeaways and Vision:

Everything in technology is time-sensitive because tech improves and evolves so fast. shows us that AI can do much more than just answer questions, run some numbers, and analyze data. Whether you’re using AI to help your business run better, or if you’re creating the next AI tool, now is the time to embrace this technology.

RS336: Claude Project Deep Dive with Alison French

mercredi 29 janvier 2025 • Durée 47:43

On today’s episode of Rogue Startups, Craig continues his AI series with founder, marketer, and Claude-user Alison French. They discuss the hesitation creators feel when working alongside AI and what Alison did to overcome that hurdle. Since then, she’s taught herself how to use Claude.ai in her creative and professional work. AI is a tool that everyone has to learn how to use.

Watch on YouTube

If you feel our podcast has benefited you and might benefit someone else, please share it with them. Also, if you have a chance, please give Rogue Startups a review on iTunes. We’ll see you next week!

Highlights from Craig and Alison’s conversation:

How creatives can use AI to improve their professional and personal lives
How to fine-tune Claude’s tone of voice:

Add files to the specific project only
- You have to feed the machine with information that matters
- Over time, working within the same project, Claude will tune itself to your prompts

How to have Claude see references and change the tone or voice

Separate and break down transcripts by prompt to hone in on specifics

Claude is like a junior copywriter: work with it and nurture it, and it will help your work go faster so you can focus on the important things. Craig’s creative process when creating content:

Get examples/models, templates, and ideas to input into your AI program of choice.
Break your content up into different functions. Go in once a week to pull out topics.

Put the time and energy into refining one meaty piece of content that you can use over and over again.

You have to focus on what makes you credible to your audience

How does your team embrace and respond to AI because at the surface it’s a risk for all of us?

How do we educate our youth now, for a future with AI?

RS335: Evaluating AI Model Performance with Stuart Grey

Épisode 335

mercredi 22 janvier 2025 • Durée 47:06

In today’s episode of Rogue Startups, Craig sits down with AI expert Dr. Stuart Grey to discuss how AI is transforming both his personal and professional life. Dr. Grey also shares how he educates his students and clients on AI applications. He believes AI will play a pivotal role in all of our futures, and while there may be hesitations, AI can be harnessed to create high-quality content and drive innovation.

Watch on YouTube

Over the next few episodes, I’ll be chatting with folks about the real ways they’re using AI in their businesses. If you’re interested in joining the conversation, hit me up (details below). But for now, here’s a breakdown of how I’m incorporating AI into my own work.

Highlights from Craig and Stuart’s conversation:

What it’s like to teach AI and machine learning at the university level
Comparing AI prompts across different platforms and analyzing results
Stuart’s AI Rules of Thumb for efficient content generation
Ethical considerations when using AI technologies
A glimpse into the near future of AI in everyday life and business
The two primary types of AI-driven content creation
How to turn basic AI-generated content into exceptional material

Takeaways and Vision

AI is integrating into our daily lives and everyone needs to learn how to leverage this powerful technology to save time and enhance productivity. Whether you’re just starting or an established professional, understanding how to work alongside AI-powered tools is key to staying ahead in your career.

Resources and Links from This Episode

Stuart Grey on LinkedIn: https://www.linkedin.com/in/stuartgrey/
Stuart Grey on X:

RS334: How AI Saves Me 10 Hours A Week

mercredi 8 janvier 2025 • Durée 15:51

Today, I’m kicking off a series on AI—how I’m using it personally and professionally to grow my business, make life easier, and operate at a higher level.

Key Ways I’m Using AI in My Business

Content Creation for Programmatic SEO
- Using OpenAI and Claude to create use case pages for Castos.
- Built a process to programmatically generate 100+ SEO landing pages using Google Sheets and templates.
- Example use case: Why Startups Should Start a Podcast for Thought Leadership.
Custom GPT for YouTube Scripts
- Created a custom GPT workflow to script our Castos YouTube videos.
- Process: Provide a topic, feed it examples, and let GPT draft outlines and scripts.
- Outcome: High-performing, 90%-ready scripts I tweak and personalize.
Building Free Marketing Tools
- Leveraging tools like Replit and Cursor to develop free tools for Castos (e.g., podcast name generator, social post creator).
- Focus: Engineering as marketing to drive traffic and lead generation.
Documenting Internal Processes
- Using Loom to record workflows (e.g., triaging support tickets).
- Leveraging AI to convert videos into detailed step-by-step process documentation (aka playbooks).
Automating Low-Level Tasks (Future Plans)
- Exploring tools like Make and Airtable for automating repetitive processes (e.g., email tagging, Slack notifications).
- Goal: Free up mental energy for high-value activities like sales, marketing, and strategy.

Takeaways and Vision

RS333: Grading My Business (and yours!)

mercredi 1 janvier 2025 • Durée 22:03

In this New Year's Eve 2024 episode, we dive into a framework for evaluating SaaS businesses across eight crucial criteria. Instead of doing a typical year-in-review or making predictions, we explore how to assess the fundamental strength and potential of your business.

Episode Highlights

Craig grades Castos (podcast hosting platform) across eight key criteria for evaluating SaaS businesses:

1. Pricing (6/10)
- Core product (podcast hosting) averages $28/month - below ideal $50+ threshold
- Production services start at $1,500/month
- Enterprise clients pay tens of thousands annually
- Mixed pricing model affects overall score

2. Churn (9/10)
- Extremely low churn rate
- Attributes success to:
- WordPress integration
- Premium pricing (no free tier)
- Strong technical reliability

3. Payment Processing Integration (4/10)
- Offers multiple monetization options:
- Castos Ads
- Castos Commerce
- Donations
- Paid subscriptions
- Private podcasting
- Limited adoption of direct monetization features
- Most customers monetize indirectly through business growth

4. Switching Costs (6/10)
- Technically easy to switch providers
- High retention due to ongoing necessity
- Perceived switching cost higher than actual

5. Technical Advantages
- WordPress integration provides unique value
- Core functionality similar to competitors
- Important lesson: Customer needs often simpler than assumed

6. Expansion Revenue (3/10)
- Limited expansion opportunities
- Most customers stay at $19/month
- Working to add upgrade opportunities
- Identified as major growth limitation

7. Established Market Need (10/10)- Clear market position- Well-understood service category- Strong product-market fit

RS332: Competing with Stripe and Hubspot (ft. Geoff Roberts)

mercredi 25 décembre 2024 • Durée 39:14

Hey everyone! Just had an awesome chat with Geoff Roberts from Outseta (outseta.com). They're doing something pretty wild - basically smashing together Stripe and HubSpot into one platform for subscription businesses. How cool is that?

Quick Hits:
- Outseta is an all-in-one platform handling payments, auth, CRM, email, and help desk
- They've got this unique setup where everyone makes $210k/year (pro-rated) and can work 1-5 days a week
- Took them 4 years to really nail the product (hey, good things take time!)

Best Parts of the Convo:
- Jeff got real about marketing struggles (who hasn't been there?)
- Turns out ChatGPT is actually sending them customers now - wild!
- We had a great debate about whether SaaS is still the golden ticket (spoiler: it's way more competitive now)
- Talked about why sometimes it's better to stick with a "pretty good" business than chase the next unicorn

Where They're Headed:
- Aiming for $10M in revenue with a lean team of about 20 people
- Shifting from being super product-focused to really pushing growth
- Geoff's been at it for 8 years and plans to keep going for 7 more

Real talk: This episode is perfect if you're building a SaaS company or thinking about bundling multiple tools together. Geoff drops some serious knowledge about what it's actually like in the trenches.

Check them out at outseta.com if you want to see what they're building!

#SaaS #Startups #Entrepreneurship

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