Donal Greene didn’t raise $100M. He didn’t even follow the startup playbook.Instead, he bootstrapped a lean team, built a better identity verification product, and forced one of his competitor’s customers to acquire him by showing them how broken their current solution was.In this episode of Decelerator, we dive into:

• How Donal built a “Minimum Lovable Product” instead of chasing MVP hype
• Why deep domain knowledge beat VC-funded noise
• What he learned replacing his founding team mid-build
• How a cold outreach turned into a full acquisition
• And what he’d do differently the next time around

This one’s for the builders who’d rather out-execute than out-raise.

📬 Tech entrepreneurship is changing fast. Join the conversation: https://decelerator.link/updates?ref=youtube

#podcast #interview #ai #startups #entrepreneur #entrepreneurship #technology #technews #artificialintelligence #innovation

📬 Tech entrepreneurship is changing fast. Join the conversation.

At the inaugural Web Summit Vancouver 2025, I sit down with JF Gauthier, founder of Startup Genome to unpack why ecosystems like those in Canada, Europe, and beyond are falling behind and what the top-performing cities are doing differently (like Philadelphia).

We dive deep into:

• Why AI is killing traditional SaaS
• How governments can seed ecosystems then get out of the way
• The real reason Canada's commercialization gap persists
• What investors should be doing in the AI-native era
• The new rules for building and scaling in 2025

Whether you're an entrepreneur, policymaker, or investor, this is your roadmap to staying relevant in the next wave of innovation.

🔗 Full Startup Genome report

📬 Tech entrepreneurship is changing fast. Join the conversation.

⁠Subscribe to my newsletter here to stay up to date on the new startup world⁠!

AI startups in 2025 are throwing out the roadmap. In this episode, investor Ryan Henry shares what he’s seeing at the frontier: agentic workflows, founder-led experimentation, and why traditional product roles are fading fast. We also revisit a debate about “vibe coding” - intuition-led building in a world of moving targets.

📍 Key Moments

• 00:00 - Introduction to Ryan Henry and his family office VC approach
• 02:40 - Ryan's fund structure: investing in other funds for deal flow
• 07:12 - Different return expectations compared to traditional VCs
• 18:30 - Debating "vibe coding": what it is and its implications
• 21:32 - The evolution of AI-assisted development capabilities
• 27:10 - Concerns about rapid prototyping vs. proper customer discovery
• 33:30 - Current YC trends: AI agents, robotics, and advanced manufacturing
• 41:55 - The state of AI agents today and what they can reliably do
• 47:38 - Building companies with anticipation of improving AI capabilities

⁠Subscribe to my newsletter here to stay up to date on the new startup world⁠!

At the Consensus 2025 conference in Toronto, I discovered something unexpected: Enron - yes that Enron - the infamous energy company that collapsed in 2001 is being revitalized with a mission to solve America's energy crisis.

Connor Gaydos, best known for creating the viral "Birds Aren't Real" movement, shares his vision for transforming the disgraced Enron brand into a trusted energy provider focused on transparency, community, and innovative solutions to fix the electrical grid.

With energy and Web3 investors, he shares his vision and journey to date, with a little bit of token malfeasance he discovered along the way.

0:00 - Consensus 2025 recap

3:01 - Meet Connor Gaydos, the new CEO of Enron

5:47 - Lessons learned from "Birds Aren't Real" and memetic marketing

8:46 - Enron's mission to fix America's energy crisis

11:12 - Innovative battery solutions to address peak energy demands

14:00 - How Web3 and community tokens fit into Enron's strategy

17:15 - Building trust with a historically distrusted brand

21:22 - The "Egg" - Enron's micro-nuclear reactor concept

24:28 - Taking on entrenched energy monopolies

29:46 - Building community through internship programs

31:31 - Lessons from cryptocurrency setbacks

33:34 - Enron's six-month roadmap to enter the Texas energy market

Connor explains how he's using memetic marketing to raise awareness about energy issues while building a legitimate business focused on battery storage, retail energy provision, and eventually micro-nuclear technology.

By attracting attention through the infamous Enron brand, he hopes to challenge the status quo in an industry that has lacked innovation and customer focus.

#startup #founder #entrepreneur #entrepreneurship #web3 #podcast

Markus shares insights on how Austria is creating a supportive ecosystem for founders, the advantages of a strong social safety net for risk-taking, and why Europe is working to change from "America innovates, China duplicates, Europe regulates" to becoming a more attractive hub for innovation.Subscribe and share your thoughts in the comments about how your local ecosystem compares!00:00:18 - Monologue: Rob's thoughts on expertise in the digital age00:06:23 - Markus introduces his roles with Austrian Startups00:07:05 - EU tech policy and the need for a unified approach00:10:43 - Challenges of talent retention in Europe00:16:03 - Austrian Startups' three main verticals of activities00:20:59 - Austria's unique ecosystem advantages and value proposition00:28:40 - Why Austria serves as a bridge between Eastern and Western Europe00:31:00 - Strong financial services and fintech presence in Austria00:34:52 - Addressing the brain drain and talent movement00:43:12 - Practical considerations of building companies in Austria00:47:26 - Balancing public grants with sustainable business models00:51:47 - Fostering entrepreneurial culture through education#techecosystem #entrepreneurship #europe #innovation #podcast #business #entrepreneur #ai #news

Early-stage startup advisory and fiduciary boards are often set up… incorrectly.Breen Sullivan, founder of The Fourth Effect, unpacks: • how the right board structure can transform early-stage companies • the untapped potential of properly structured advisory relationships • why experienced executives often struggle to provide value to startups, and how they can, if set up correctlyIf you’re a founder looking to build strategic advisory relationships, or an executive wanting to break into the board ecosystem, this episode offers invaluable insights on maximizing these relationships for mutual benefit.Timestamps:0:00 – Introduction & SXSW highlights3:29 – Intro to Breen Sullivan & The Fourth Effect5:43 – How The Fourth Effect’s marketplace works10:52 – Building trust in a board-matching marketplace15:09 – The evolution of advisory relationships in startups24:03 – Understanding the three types of board seats32:42 – Why startups need proper board structures38:20 – The challenges corporate executives face when joining startup boards48:11 – The Fourth Effect’s future and investment plans👍 Like, subscribe, and share if you found this conversation valuable! What board structures have worked for your startup? Share your experiences in the comments below.#startups #founder #entrepreneur #entrepreneurship #podcast #interview

Freight logistics quietly powers our economy - until it breaks. FreightSimple is a B2B logistics company that solves for these shipping problems. To that end, this episode we recorded before the trade war started in earnest, so perhaps I need to have Natasha Ross, the cofounder, on weekly to follow the twists and turns in her business.

The business may seem dry - spoiler alert: that's the point - but it ain't. We covered the typical startup stuff (problem, solution, etc.), but Natasha was unusually candid about how she looks at her business. Her cofounder exited to Apple previously, which creates an interesting dynamic. I asked her whether she was shooting for an acquisition or how did she define success, and she answered thoughtfully.

I also felt the need in the monologue to talk about enshittification and where I think it will show up next.

In this episode we cover:

• The absurdity of freight logistics: "You'd email or call around, hoping someone replies before your shipment misses the truck."
• The startup reality check: "Initially, the market was allergic to tech; now they can't get enough."
• Natasha’s best lesson: "Solve the boring stuff—complexity hides opportunity."
• How to earn an industry's trust and Natasha's advice for entrepreneurs.

00:02:00 – Interview begins: Natasha Ross from FreightSimple

00:08:30 – Life before FreightSimple: struggles with manual logistics

00:14:52 – Empowering businesses to simplify freight decisions

00:22:37 – Why solving logistics problems is uniquely rewarding

00:29:34 – Behind-the-scenes: automating freight bookings

00:37:08 – Eliminating costly mistakes in shipping logistics

00:46:12 – Overcoming startup challenges in resistant industries

00:54:26 – Gaining industry trust: lessons from FreightSimple’s growth

01:02:10 – Natasha’s advice for entrepreneurs navigating complex industries

Let's get ... deeper... into AI startups + AI business models + where Deepseek fits with a product-focused family office VC's perspective. We go beyond the freak out headlines and get into what's happening, how the models and DeepSeek work, and how to think about your AI startup.

01:00 - A family office VC’s AI perspective
04:30 - AI startups: How investors really think
08:45 - AI as a business: Feature vs. product
12:20 - How AI models actually work and think
18:10 - The business models of AI and OpenAI’s strategy
24:00 - Startups vs. incumbents: How to win in the AI era
30:15 - DeepSeek’s role and where it fits in
35:40 - AI's real economic moats
40:25 - What’s next for AI startups?

Today's guest is Melissa Kwan, founder of eWebinar, a company that turns videos into interactive webinars. She's an outspoken bootstrapper, and her journey and perspectives are fascinating. Enjoy!

Director, producter, co-creator: Christopher Mudiappahpillai
Founder, host, co-creator: Rob Kenedi
Good jokes: Paul Bates
Bad jokes: Rob Kenedi

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00:04:03 - Introduction of Melissa Kwan
- Rob introduces Melissa Kwan, founder of eWebinar, and mentions her journey as a bootstrapper.

00:04:14 - Overview of eWebinar
- Melissa explains that eWebinar automates webinars by turning videos into interactive webinars, particularly useful for onboarding and training.

00:04:52 - Features of eWebinar
- The platform includes interactive elements like polls, questions, and asynchronous chat for real-time or later responses.

00:05:11 - Competitors
- Melissa identifies competitors such as EverWebinar and EasyWebinar, noting that most focus on live webinars while eWebinar specializes in automation.

00:06:02 - Previous Company
- Melissa discusses her previous company, Spacio, which she exited in 2019, and reflects on her revelations before starting eWebinar.

00:07:39 - Media's Measure of Success
- Melissa emphasizes that media recognition does not equate to personal success, highlighting the importance of personal metrics over external validation.

00:08:25 - Journey to Understanding Success
- Melissa shares her journey of moving to New York and the pressures of startup culture, leading to her realization about the nature of success.

00:10:20 - The Impact of Not Raising Funds
- Melissa reflects on how not getting funded allowed her to build a profitable business without the pressures of investor expectations.

00:11:05 - Debt and Financial Struggles
- Melissa discusses her financial struggles, including debt from her previous startup, and the mental toll it took on her.

00:17:02 - Mental Preparation for eWebinar
- Melissa describes her mental state when starting eWebinar, including fears of returning to previous struggles and the need for a positive mindset.

00:25:02 - Non-Negotiables for the New Company
- Melissa created a list of non-negotiables for her next venture, which guided her decision-making process.

00:30:05 - Purple Ocean Strategy
- Melissa explains her approach to eWebinar as a "purple ocean" opportunity, improving upon existing solutions rather than creating something entirely new.

00:32:11 - Friends and Family Investment
- Melissa discusses taking friends and family investments and the importance of transparency regarding the risks involved.

00:35:07 - Structure of eWebinar's Investment
- Melissa explains how eWebinar was structured to allow for dividends based on investment percentage, which differs from traditional VC models.

00:36:05 - Drawbacks of Bootstrapping
- Melissa acknowledges the challenges of bootstrapping, including the need for side hustles and the distractions they bring.

00:40:39 - Speed to Market
- Melissa reflects on the speed of bringing eWebinar to market, emphasizing the importance of having a revenue-generating product from the start.

Our first episode of Decelerator with Rob Kenedi, featuring Jennifer Yip of Lunch Money.