Ep 64: The Last 90 Days: Why Looking Back Is Your Biggest Growth Strategy episode artwork

EPISODE · Jun 11, 2026 · 21 MIN

Ep 64: The Last 90 Days: Why Looking Back Is Your Biggest Growth Strategy

from Revenue Rewired · host Jay Feitlinger & Sarah Shepard | B2B Growth Experts

Everyone's laser-focused on what's coming in the next 90 days, but Jay and Sarah are making a case for something most business owners skip entirely: a real look at what just happened. In this episode, they break down why so many companies keep missing their quarterly targets, even when the numbers feel completely reasonable going in. Jay shares a candid story from a client who was exceeding profit goals yet consistently falling short on revenue forecasts, and the uncomfortable truth about where the breakdown was actually happening. And fixing it starts with slowing down long enough to look back before you sprint forward.KEY TAKEAWAYSYour team isn't the problem. Quarterly misses often trace back to a forecasting process that doesn't have the right people in the room, and no amount of accountability will fix a broken foundation.The visionary CEO blind spot is real. When there's no operationally grounded voice in planning conversations, revenue targets can drift into wishful thinking fast.Doing a retro doesn't have to be painful. A simple template and a safe space for your team to debrief can turn past projects into better scoping decisions and more accurate numbers.Cash flow is the number you're probably underweighting. Revenue growth looks great until you realize profit and expenses weren't part of the equation from the start.The patterns you ignore this quarter will show up again next quarter. If something's consistently broken, it won't fix itself just because the calendar changed.EPISODE CHAPTERS00:25 - Jay's Flagstaff escape plan and why Arizona summers hit different01:20 - Why June has a way of blindsiding business owners every year02:10 - The case for making the last 90 days your most important ones03:35 - A client story: killing it on profit, missing badly on revenue05:45 - How finger-pointing gets in the way of fixing the actual problem07:30 - Driving through water: what a Google Maps glitch taught Jay about goal-setting08:17 - Why stepping back feels like going backward (and why that's the point) 09:16 - The visionary CEO vs. the operational realist: why you need both11:57 - You can't look forward and backward at the same time 13:38 - What's actually worked: removing friction and fixing the foundation first 15:00 - Three revenue buckets StringCan uses to build quarterly goals 18:10 - The number Jay forgot (and why Sarah never does) 19:24 - How to make retros something your team will actually do 21:04 - Wrapping up and staying cool out thereSEO KEYWORDSquarterly business planning, Q3 revenue strategy, B2B revenue growth, business retrospective, quarterly goal setting, revenue forecasting, EOS business model, COO vs CEO roles, cash flow management, revenue leaks, business operations, mid-market growth strategy, sales and marketing alignment, quarterly retro template, business planning mistakesHOSTSJay Feitlinger is the CEO of StringCan Interactive and the author of Family 2.0. He brings a visionary, growth-first perspective to every conversation about revenue strategy and business leadership. LinkedIn: https://www.linkedin.com/in/jayfeitlinger/Sarah Shepard is the COO of StringCan Interactive and the operational counterweight every visionary leader needs. She keeps the numbers honest and the plans grounded. LinkedIn: https://www.linkedin.com/in/sarahshepardcoo/ABOUT REVENUE REWIRED Revenue Rewired is a podcast for B2B owners, marketers, and sales leaders who want to grow revenue with more intention and less guesswork. Every episode delivers no-fluff insights built for mid-market companies ready to scale smart. Hosted by Jay Feitlinger and Sarah Shepard of StringCan Interactive.Get the Revenue Rewired book: amazon.com/Revenue-Rewired Read the newsletter:https://www.linkedin.com/pulse/work-you-keep-restarting-calling-strategy-jay-feitlinger-moizc Send your questions: [email protected] Visit: www.stringcaninteractive.com

Everyone's laser-focused on what's coming in the next 90 days, but Jay and Sarah are making a case for something most business owners skip entirely: a real look at what just happened. In this episode, they break down why so many companies keep missing their quarterly targets, even when the numbers feel completely reasonable going in. Jay shares a candid story from a client who was exceeding profit goals yet consistently falling short on revenue forecasts, and the uncomfortable truth about where the breakdown was actually happening. And fixing it starts with slowing down long enough to look back before you sprint forward.KEY TAKEAWAYSYour team isn't the problem. Quarterly misses often trace back to a forecasting process that doesn't have the right people in the room, and no amount of accountability will fix a broken foundation.The visionary CEO blind spot is real. When there's no operationally grounded voice in planning conversations, revenue targets can drift into wishful thinking fast.Doing a retro doesn't have to be painful. A simple template and a safe space for your team to debrief can turn past projects into better scoping decisions and more accurate numbers.Cash flow is the number you're probably underweighting. Revenue growth looks great until you realize profit and expenses weren't part of the equation from the start.The patterns you ignore this quarter will show up again next quarter. If something's consistently broken, it won't fix itself just because the calendar changed.EPISODE CHAPTERS00:25 - Jay's Flagstaff escape plan and why Arizona summers hit different01:20 - Why June has a way of blindsiding business owners every year02:10 - The case for making the last 90 days your most important ones03:35 - A client story: killing it on profit, missing badly on revenue05:45 - How finger-pointing gets in the way of fixing the actual problem07:30 - Driving through water: what a Google Maps glitch taught Jay about goal-setting08:17 - Why stepping back feels like going backward (and why that's the point) 09:16 - The visionary CEO vs. the operational realist: why you need both11:57 - You can't look forward and backward at the same time 13:38 - What's actually worked: removing friction and fixing the foundation first 15:00 - Three revenue buckets StringCan uses to build quarterly goals 18:10 - The number Jay forgot (and why Sarah never does) 19:24 - How to make retros something your team will actually do 21:04 - Wrapping up and staying cool out thereSEO KEYWORDSquarterly business planning, Q3 revenue strategy, B2B revenue growth, business retrospective, quarterly goal setting, revenue forecasting, EOS business model, COO vs CEO roles, cash flow management, revenue leaks, business operations, mid-market growth strategy, sales and marketing alignment, quarterly retro template, business planning mistakesHOSTSJay Feitlinger is the CEO of StringCan Interactive and the author of Family 2.0. He brings a visionary, growth-first perspective to every conversation about revenue strategy and business leadership. LinkedIn: https://www.linkedin.com/in/jayfeitlinger/Sarah Shepard is the COO of StringCan Interactive and the operational counterweight every visionary leader needs. She keeps the numbers honest and the plans grounded. LinkedIn: https://www.linkedin.com/in/sarahshepardcoo/ABOUT REVENUE REWIRED Revenue Rewired is a podcast for B2B owners, marketers, and sales leaders who want to grow revenue with more intention and less guesswork. Every episode delivers no-fluff insights built for mid-market companies ready to scale smart. Hosted by Jay Feitlinger and Sarah Shepard of StringCan Interactive.Get the Revenue Rewired book: amazon.com/Revenue-Rewired Read the newsletter:https://www.linkedin.com/pulse/work-you-keep-restarting-calling-strategy-jay-feitlinger-moizc Send your questions: [email protected] Visit: www.stringcaninteractive.com

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Ep 64: The Last 90 Days: Why Looking Back Is Your Biggest Growth Strategy

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This episode was published on June 11, 2026.

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Everyone's laser-focused on what's coming in the next 90 days, but Jay and Sarah are making a case for something most business owners skip entirely: a real look at what just happened. In this episode, they break down why so many companies keep...

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