Use AI not just to align with your thinking, but to challenge it. Prompting AI to write from a critical perspective, like a competitor or a tough stakeholder, can reveal unexpected insights and blind spots.
This practice forces you to anticipate objections and shows where your messaging, assumptions, or pitch might be weak.
Key takeaway: Make AI your sparring partner. Purposefully prompting it to disagree is the fastest way to strengthen your ideas and find your next breakthrough.
Contact Us:
Email: podcast@stringcaninteractive.com
Website: www.stringcaninteractive.com
Reach out to the hosts on LinkedIn:
Jay Feitlinger: https://www.linkedin.com/in/jayfeitlinger/
Sarah Shepard: https://www.linkedin.com/in/sarahshepardcoo/
Buy the Revenue Rewired book: https://www.amazon.com/Revenue-Rewired-Identify-Leaks-Costing-ebook/dp/B0FST7JCXQ
What if you could preview how your client will respond before you hit send? In this episode of Two-Minute AI Tips, Sarah shares how to structure AI to simulate client feedback, and why it’s one of the most underrated uses of generative tech.
In this episode, you’ll learn:
Your best prompt might not be about content, it might be about context.
Contact Us:
Email: podcast@stringcaninteractive.com
Website: www.stringcaninteractive.com
Reach out to the hosts on LinkedIn:
Jay Feitlinger: https://www.linkedin.com/in/jayfeitlinger/
Sarah Shepard: https://www.linkedin.com/in/sarahshepardcoo/
You’ve seen companies pour six figures into a website… only to let it decay the second it launches. You’ve watched teams treat a major brand asset like a “set it and forget it” project. And thanks to AI, you’re now watching websites become one of the most important signals in your entire revenue engine.
In this episode, Sarah and Jay break down the fastest ways companies ruin their website investment, from outdated content that undermines credibility to neglected ADA issues, aging design, messy navigation, and the hidden AI implications no one is talking about. They unpack why websites built during the pandemic are now showing their age, how AI is resurrecting the importance of strong on-site messaging, and what actually happens to revenue when a site stops reflecting who you are today.
In this episode, you’ll learn:
If you’ve been wondering whether your website still earns its keep, this episode gives you the clarity (and honesty) you need to protect your investment, and rebuild it the right way if you don’t.
Contact Us:
Email: podcast@stringcaninteractive.com
Website: www.stringcaninteractive.com
Reach out to the hosts on LinkedIn:
Jay Feitlinger: https://www.linkedin.com/in/jayfeitlinger/
Sarah Shepard: https://www.linkedin.com/in/sarahshepardcoo/
Buy the Revenue Rewired book: https://www.amazon.com/Revenue-Rewired-Identify-Leaks-Costing-ebook/dp/B0FST7JCXQ
Ever get great output from AI, only to realize it won’t fly with your team? In this episode of Two-Minute AI Tips, Sarah unpacks why AI misses internal nuance, and how to prompt like a strategist, not just a taskmaster.
In this episode, you’ll learn:
AI can’t navigate your team. That’s your job. Lead accordingly.
Contact Us:
Email: podcast@stringcaninteractive.com
Website: www.stringcaninteractive.com
Reach out to the hosts on LinkedIn:
Jay Feitlinger: https://www.linkedin.com/in/jayfeitlinger/
Sarah Shepard: https://www.linkedin.com/in/sarahshepardcoo/
You’ve seen sales and marketing clash. You’ve lived the messy handoffs. And you’ve probably wondered who should actually own what inside your revenue engine.
In this episode, Sarah and Jay unpack the real friction point between marketing and sales, where one ends, the other begins, and why the line between them is a lot gooier than anyone wants to admit. From cold email debates to personalization rabbit holes to the “who writes what” showdown that sparked this episode, they pull apart the blurry middle where most companies lose speed, clarity, and opportunities.
In this episode, you’ll learn:
If you’ve ever felt like your teams are stepping on each other’s toes, this episode will show you how to tighten the handoff, reduce the noise, and build a revenue flow that actually works.
Contact Us:
Email: podcast@stringcaninteractive.com
Website: www.stringcaninteractive.com
Reach out to the hosts on LinkedIn:
Jay Feitlinger: https://www.linkedin.com/in/jayfeitlinger/
Sarah Shepard: https://www.linkedin.com/in/sarahshepardcoo/
Buy the Revenue Rewired book: https://www.amazon.com/Revenue-Rewired-Identify-Leaks-Costing-ebook/dp/B0FST7JCXQ
Not all overuse looks like overuse. In this episode of Two-Minute AI Tips, Sarah calls out the quiet addiction leaders are developing to AI, and how to tell when you’ve crossed from leverage into dependence.
In this episode, you’ll learn:
Your judgment isn’t optional. AI should support it, not substitute it.
Contact Us:
Email: podcast@stringcaninteractive.com
Website: www.stringcaninteractive.com
Reach out to the hosts on LinkedIn:
Jay Feitlinger: https://www.linkedin.com/in/jayfeitlinger/
Sarah Shepard: https://www.linkedin.com/in/sarahshepardcoo/
Ever looked at an agency proposal and thought, “Why am I paying for account management?”
Account management shows up on nearly every agency proposal, but most people do not know what it actually includes. It looks vague. It looks optional. It looks like something you should not have to pay for.
In this episode, Sarah and Jay explain the real purpose of the account management line item and why it is essential to keeping your marketing investment productive. They break down what is included in that cost, why it exists in the first place, and how strong account management creates speed, clarity, and revenue impact for your company.
In this episode, you will learn:
If you have ever considered removing this line from a proposal, this episode will clarify what you would lose and why it matters for your pipeline.
Contact Us:
Email: podcast@stringcaninteractive.com
Website: www.stringcaninteractive.com
Reach out to the hosts on LinkedIn:
Jay Feitlinger: https://www.linkedin.com/in/jayfeitlinger/
Sarah Shepard: https://www.linkedin.com/in/sarahshepardcoo/
Buy the Revenue Rewired book: https://www.amazon.com/Revenue-Rewired-Identify-Leaks-Costing-ebook/dp/B0FST7JCXQ
ChatGPT forgetting what you said five prompts ago? In this episode of Two-Minute AI Tips, Sarah breaks down why AI struggles with long conversations, and what smart users do instead.
In this episode, you’ll learn:
Don’t expect it to follow the thread. Build the structure that keeps it on track.
Contact Us:
Email: podcast@stringcaninteractive.com
Website: www.stringcaninteractive.com
Reach out to the hosts on LinkedIn:
Jay Feitlinger: https://www.linkedin.com/in/jayfeitlinger/
Sarah Shepard: https://www.linkedin.com/in/sarahshepardcoo/
Not sure what makes an AI “agent” different from a chatbot? You’re not alone. In this episode of Two-Minute AI Tips, Sarah explains what separates talk from action, and why agents are the future of real AI productivity.
In this episode, you’ll learn:
If you want AI that actually does things, this is where it starts.
Contact Us:
Email: podcast@stringcaninteractive.com
Website: www.stringcaninteractive.com
Reach out to the hosts on LinkedIn:
Jay Feitlinger: https://www.linkedin.com/in/jayfeitlinger/
Sarah Shepard: https://www.linkedin.com/in/sarahshepardcoo/
You want your message to stand out. Your audience just wants quiet. And somewhere in between, your buyers stopped listening.
In this episode, Jay and Sarah unpack why so many teams are chasing attention in oversaturated channels, and how platforms like Reddit are quietly becoming the new places where real conversations (and buying signals) happen. They talk about the shift from noise to nuance, the fatigue of LinkedIn spam, and how decision-weary audiences are forcing brands to get clearer, simpler, and more focused.
In this episode, you’ll learn:
If your team keeps casting into the same noisy waters, this episode might just show you where the new fish are actually swimming.
Contact Us:
Email: podcast@stringcaninteractive.com
Website: www.stringcaninteractive.com
Reach out to the hosts on LinkedIn:
Jay Feitlinger: https://www.linkedin.com/in/jayfeitlinger/
Sarah Shepard: https://www.linkedin.com/in/sarahshepardcoo/
Buy the Revenue Rewired book: https://www.amazon.com/Revenue-Rewired-Identify-Leaks-Costing-ebook/dp/B0FST7JCXQ
Ever wonder why ChatGPT, Perplexity or Claude fall apart playing chess? In this episode of Two-Minute AI Tips, Sarah shares what happened when she relied on Claude mid-game, and why language models will never match a real chess engine.
In this episode, you’ll learn:
If you’ve ever mistaken confidence for competence, this episode is your checkmate.
Contact Us:
Email: podcast@stringcaninteractive.com
Website: www.stringcaninteractive.com
Reach out to the hosts on LinkedIn:
Jay Feitlinger: https://www.linkedin.com/in/jayfeitlinger/
Sarah Shepard: https://www.linkedin.com/in/sarahshepardcoo/
We’ve been thinking a lot about how leadership has changed. We’re faster. Smarter. More data-driven than ever. And somehow, we’ve forgotten how to trust ourselves.
In this solo episode, Sarah talks about what happens when we trade instinct for validation, when every decision needs a dashboard, a spreadsheet, or a prompt before we move. She’ll share why clarity and certainty aren’t the same thing, and how to rebuild the instinct that data can’t replicate.
In this episode, you’ll learn:
If you’ve been waiting for one more report before acting on what you already know is right, this might be the reminder you didn’t know you needed.
Contact Us:
Email: podcast@stringcaninteractive.com
Website: www.stringcaninteractive.com
Reach out to the hosts on LinkedIn:
Jay Feitlinger: https://www.linkedin.com/in/jayfeitlinger/
Sarah Shepard: https://www.linkedin.com/in/sarahshepardcoo/
Buy the Revenue Rewired book: https://www.amazon.com/Revenue-Rewired-Identify-Leaks-Costing-ebook/dp/B0FST7JCXQ
Stop waiting for the perfect output. In this episode of Two-Minute AI Tips, Sarah explains why power users don’t rely on one response, they curate, compare, and remix. Because with AI, the real magic isn’t in the prompt. It’s in the pick.
In this episode, you’ll learn:
If you’ve been disappointed by “meh” responses, this one’s your reframe.
Contact Us:
Email: podcast@stringcaninteractive.com
Website: www.stringcaninteractive.com
Reach out to the hosts on LinkedIn:
Jay Feitlinger: https://www.linkedin.com/in/jayfeitlinger/
Sarah Shepard: https://www.linkedin.com/in/sarahshepardcoo/
Your roadmap is opinionated. Your pipeline is impatient. Your competitors are running experiments tonight.
In this episode, Sarah and Jay explain why experimentation is the operating system of modern growth, not a marketing hobby. They deliver a ruthless, revenue-first playbook: how to pick hypotheses that map to pipeline, size tests so results actually mean something, force winners into the business, and use AI to surface ideas and speed analysis without sacrificing rigor.
In this episode, you’ll learn:
If you skip deliberate testing, you’re letting everyone else learn faster, this episode gives you the playbook to catch up and pull ahead.
Contact Us:
Email: podcast@stringcaninteractive.com
Website: www.stringcaninteractive.com
Reach out to the hosts on LinkedIn:
Jay Feitlinger: https://www.linkedin.com/in/jayfeitlinger/
Sarah Shepard: https://www.linkedin.com/in/sarahshepardcoo/
Buy the Revenue Rewired book: https://www.amazon.com/Revenue-Rewired-Identify-Leaks-Costing-ebook/dp/B0FST7JCXQ
AI isn’t getting better, because you’re not teaching it. In this episode of Two-Minute AI Tips, Sarah explains why silently fixing AI output stalls progress, and what leaders must do to turn rewrites into real improvement.
In this episode, you’ll learn:
If you’re tired of AI “not getting it,” this episode shows you why, and how to fix it.
Contact Us:
Email: podcast@stringcaninteractive.com
Website: www.stringcaninteractive.com
Reach out to the hosts on LinkedIn:
Jay Feitlinger: https://www.linkedin.com/in/jayfeitlinger/
Sarah Shepard: https://www.linkedin.com/in/sarahshepardcoo/
You wanted results yesterday. Your boss wants more leads tomorrow. But your agency? They're asking you to slow down.
In this episode, Jay and Sarah unpack why strategy feels slow, but is actually the fastest path to sustainable growth. From TikTok tree surgeons to Wile E. Coyote references, they break down why “just doing something” often backfires, and how external partners can help you see the real issues under the surface.
In this episode, you’ll learn:
If strategy feels like a luxury you don’t have time for, this episode might just change your mind.
Contact Us:
Email: podcast@stringcaninteractive.com
Website: www.stringcaninteractive.com
Reach out to the hosts on LinkedIn:
Jay Feitlinger: https://www.linkedin.com/in/jayfeitlinger/
Sarah Shepard: https://www.linkedin.com/in/sarahshepardcoo/
Buy the Revenue Rewired book: https://www.amazon.com/Revenue-Rewired-Identify-Leaks-Costing-ebook/dp/B0FST7JCXQ
Everyone’s talking about prompts. But the real power move? Structuring the data no one else has. In this episode of Two-Minute AI Tips, Sarah breaks down the winning combo of proprietary data and AI, and why infrastructure, not novelty, is your edge.
In this episode, you’ll learn:
If you want a moat AI can actually defend, it starts with your data.
Contact Us:
Email: podcast@stringcaninteractive.com
Website: www.stringcaninteractive.com
Reach out to the hosts on LinkedIn:
Jay Feitlinger: https://www.linkedin.com/in/jayfeitlinger/
Sarah Shepard: https://www.linkedin.com/in/sarahshepardcoo/
You’ve got a curious prospect. They like your work. They’re vibing with your team. But when you ask what they’re trying to achieve... crickets.
In this episode, Jay and Sarah break down why the single most important thing in your sales process isn’t a deck, a demo, or a discount, it’s clarity.
You’ll learn how they use one make-or-break question to qualify real opportunities, stop chasing vague leads, and get buyers to define success before a proposal ever hits their inbox.
In this episode, you’ll learn:
If your sales process feels stuck, bloated, or aimless, this one’s your reset.
Contact Us:
Email: podcast@stringcaninteractive.com
Website: www.stringcaninteractive.com
Reach out to the hosts on LinkedIn:
Jay Feitlinger: https://www.linkedin.com/in/jayfeitlinger/
Sarah Shepard: https://www.linkedin.com/in/sarahshepardcoo/
AI writing is getting smoother, but not smarter. In this episode of Two-Minute AI Tips, Sarah breaks down the subtle clues that reveal when something was written by a model, not a human, and why removing too much “mess” makes your message fall flat.
In this episode, you’ll learn:
If your writing feels too clean to connect, this one’s for you.
Contact Us:
Email: podcast@stringcaninteractive.com
Website: www.stringcaninteractive.com
Reach out to the hosts on LinkedIn:
Jay Feitlinger: https://www.linkedin.com/in/jayfeitlinger/
Sarah Shepard: https://www.linkedin.com/in/sarahshepardcoo/
Buy the Revenue Rewired book: https://www.amazon.com/Revenue-Rewired-Identify-Leaks-Costing-ebook/dp/B0FST7JCXQ
Everyone wants faster sales cycles.
But what if that’s not the smartest move?
In this episode, Sarah and Jay challenge the assumption that a shorter sales process is always better. Drawing on their own experience with HubSpot, and their journey refining StringCan’s intake, they explore the value of longer business development cycles that actually build trust, answer real questions, and set the foundation for stronger client partnerships.
If long qualification cycles are critical in SaaS, why are service-based businesses skipping them, and then wondering why retention suffers?
In this episode, you’ll learn:
If your sales process is all speed and no substance, this episode will make you rethink everything.
Contact Us:
Email: podcast@stringcaninteractive.com
Website: www.stringcaninteractive.com
Reach out to the hosts on LinkedIn:
Jay Feitlinger: https://www.linkedin.com/in/jayfeitlinger/
Sarah Shepard: https://www.linkedin.com/in/sarahshepardcoo/