Glenn Gow, The Scaling Executive Coach and host of The Scaling Executive Podcast, sat down with Ryan Austin, founder and CEO of Cognota, to unpack what actually separates founders who build lasting companies from those who quietly kill them. Austin has founded five companies, bootstrapped his way out of a university dorm room, raised venture capital, and completed successful exits. His core message: the biggest threat to your company is not the market. It is you.
For CEOs trying to grow past their current ceiling, Austin’s framework is direct. Get patient. Get aligned. Then get out of the way at the right time.
This episode is for CEOs and founders wrestling with when to delegate, how to build alignment after chaos, and why their own impatience may be the biggest risk to their company’s survival.
Key Takeaways
- Impatience kills more companies than markets do. Founders who exit too early or pivot when they should stay are applying a false growth standard — most technology companies take five to ten years to reach meaningful scale, not twelve months.
- CEOs who skip the post-quarter alignment conversation pay for it the next quarter. Taking two days to talk about the ugly stuff as a leadership team is what prevents chaos from compounding.
- Connecting every L&D dollar and hour to the CEO’s stated priorities is a fiduciary responsibility. Saying yes to work that does not link to the top three to five initiatives produces poor ROI and damages credibility as a business leader.
- Delegation of authority is a reward for demonstrated performance, not an act extended simply because a hire was made. When performance is absent, the CEO’s job is to get back in the weeds.
- Cognota CEO Ryan Austin asked his new Chief Revenue Officer if he should even attend the weekly sales meeting. The CRO said no. That is what healthy CEO delegation looks like.
Why Patient Founders Build Bigger Companies
Think about the last time you saw a headline about a startup hitting $100 million in revenue in under a year. Lovable. Replit. The names change, but the story stays the same. Fast growth, viral curve, category dominance overnight.
Here is the reality you do not see: those companies are a rounding error.
Ryan Austin learned this the hard way. He started a company in his dorm room. In its first week, it generated $10,000 in revenue. By most measures, that is a strong start. But Austin killed it before it had a chance to grow.
“Because it didn’t do a million dollars within its first year, I thought that it was just a bad business,” Austin said. “I killed it without having the insights that this was actually very successful and you should keep going. So just not having that knowledge and the right expectations hurt that business.”
The lesson runs deeper than one failed startup. Austin points to Docebo, a learning management company built by a schoolteacher, as the model most founders do not study.
“It took them like 10 years to break through the million dollar ARR mark. And then once they did that, they started to get the scale, but it took them the first 10 years to figure that out. And that’s more of the norm success story that you hear about in technology companies.”
If you are benchmarking your company against the 0.1% of outliers, you will make decisions built on a false standard. You will exit too early, pivot when you should stay, or abandon a business that is quietly succeeding.
Austin’s principle is blunt: “Businesses don’t die. The entrepreneurs kill them. A lot of the times they died because of foolish mistakes or being impatient as an entrepreneur.”
Set expectations that match reality. Five to ten years to build a billion-dollar company is not failure. It is the norm.
CEOs Build Alignment by Confronting What Went Wrong
Ryan Austin, CEO of Cognota, identifies alignment failure as the most consistent blind spot he sees in growing companies. As a team moves fast, things break. People form different views of what happened and why. Chaos builds in the gaps between functions. And most companies keep moving instead of stopping to address it.
The fix is not complicated. It is just uncomfortable.
“What happens when you start moving quickly, especially with a leadership team, is that things start to break and everybody starts to have different ideas and things get chaotic,” Austin said. “But most companies don’t take the time to focus on that chaos. All it takes is when you start missing goals or even if you’re celebrating successes… just means taking a couple days to do that offsite and being brave enough and vulnerable enough as a leadership team to talk about the ugly stuff.”
This is what a quarterly planning process actually requires. Not just goal-setting for the next 90 days. A real post-mortem on the last 90. What broke? Who owns it? What do we fix?
Austin is direct about what this costs the CEO personally: “This is very exhausting and tiring for a CEO because everybody points the finger this was Ryan’s fault or this is the CEO’s fault. And you kind of got to take it on the chin.”
The payoff only follows when the CEO absorbs the blame publicly and creates enough psychological safety for the leadership team to name the real problems. When both conditions are present, Austin says the outcome is consistent: “Once you spend a full day talking about the ugly stuff and how we can get better at doing those things and getting to the truth, the truth that will make us better, then the magic starts happening where you start building back up fully aligned to execute the next quarter focused on the truth, focused on the areas of ugliness that we’re going to fix together as a fully aligned leadership team.”
Without a CEO willing to take the blame and hold space for that honesty, the offsite produces consensus without truth — and the next quarter compounds the same broken assumptions.
If you skip this step, you execute the next quarter with the same broken assumptions. You just execute them faster.
L&D Leaders Operate Strategically by Saying No First
Austin built Cognota to solve a specific problem: learning and development teams in large enterprises are stuck in a reactive, order-taking role. They say yes to everyone. They build programs on request. They end up measuring activity instead of business impact.
His prescription starts with a principle most L&D leaders find uncomfortable: start with no.
“If you’re a leader of a learning function, a talent development function, an HR function… if you work for a company, so an enterprise or a for-profit company… you have a fiduciary responsibility like everybody else to make good investments for the business. That means good investments with time and good investments with money.”
The test is simple. Your CEO stood on stage and named the three to five initiatives that matter most this year. If your work does not connect to those initiatives, Austin says you are already failing.
“If you go and work on anything else outside of those five areas that your CEO stood up, took the time to stand up on stage about, say they’re losing sleep about it and they need your help to accomplish these, and you do anything else with your time or your money than those five things, then you’re failing automatically as a business professional or a business leader.”
He has empathy for why this is hard. L&D professionals are wired to help. Someone walks in with a request, and the instinct is to say yes. But saying yes with time and money commits resources to work that will produce no measurable business return.
“If you say yes to that, you’ve committed money and time, and now you’re responsible for delivering those results. And if it’s not aligned to the business impact to begin with, you’re going to have poor ROI and look poorly as a business leader.”
The reframe: you will say yes. But only to work that connects to what the business actually needs. Everything else gets a no.
CEOs Delegate Authority After New Executives Earn It
Ryan Austin, founder of five companies and CEO of Cognota, made a specific move when he hired a Chief Revenue Officer: he showed up to the weekly sales strategy meeting, waited until the end, and then asked whether he should still be in the room.
“Hey, I don’t know if you still want me here in this meeting anymore. I’m happy to do it and be here. Or you can delete me off of the invite and invite me into these meetings when you think I can add value to the team.”
The CRO said goodbye. Austin called it a growth moment.
But getting to that moment required something first: trust built through demonstrated performance, not just through the fact of being hired. A revenue advisor working with Cognota before the hire made a point Austin found clarifying.
“There’s this saying about hire good people and get out of the way. And his perspective is it’s instead of that, it’s like a pizza like this. And the reality is you should flip it like this, which means you come in and at the top of the pizza you have the pepperoni slices… That’s your front line people. If you want me to trust you and get out of the way, you have to prove and build trust with me.”
The standard is clear: you hired someone, you did references, you made a judgment call. But trust is still earned through actual performance, not assumed. If the performance is not there, the CEO’s job is to get back in the weeds.
“If it’s not going right, don’t ask me not to get in the weeds because my job is to get in the weeds to make sure that the company is healthy.”
For new executives, this framework sets fair expectations. It removes the anxiety of wondering whether the CEO trusts you. You demonstrate performance. You earn autonomy. The hand-off follows evidence, not optimism.
For CEOs, it prevents the most painful hiring scenario: doing the homework, making the hire, stepping back, and watching things fall apart because you got out of the way before you had any reason to.
How CEOs Apply Austin’s Frameworks to Scale Past Their Own Ceiling
The four frameworks Austin articulates across this episode form a complete operating system for founders who want to build lasting companies without destroying them in the process. Each principle below is drawn from a specific moment in Austin’s experience — not a general theory.
| Principle | What it means in practice | Named evidence from this episode |
| Impatience kills companies faster than markets do | Founders who benchmark against outlier growth curves abandon businesses that are quietly succeeding. The accurate standard is 5 to 10 years, not 12 months. | Austin shut down a dorm-room company generating $10,000 in its first week because it did not hit $1 million in year one. He later identified that decision as the mistake, not the business. |
| Post-quarter truth-telling requires the CEO to absorb blame publicly | Alignment offsites only work when the CEO creates enough psychological safety for the leadership team to name what actually broke. Consensus without that safety produces the same broken quarter, executed faster. | Austin describes spending a full day on “the ugly stuff” with his Cognota leadership team as the moment that unlocks full execution alignment in the following quarter. |
| L&D fiduciary discipline means connecting every dollar and hour to the CEO’s stated priorities | Saying yes to requests that do not connect to the CEO’s top three to five initiatives is not helpfulness — it is a misallocation of business resources that produces poor ROI and damages the L&D leader’s credibility. | Austin built Cognota specifically to solve the pattern he saw across large enterprises: L&D teams measuring activity instead of business impact because they never learned to say no. |
| Delegation follows demonstrated performance, not the fact of hiring | CEOs who step back before a new executive has proven performance create the conditions for quiet failure. The hand-off of authority is a reward for evidence, not an act of optimism. | Austin asked his new CRO to remove him from the weekly sales meeting only after the CRO demonstrated competence. Before that point, Austin’s presence was the safeguard, not the obstacle. |
Quotes from This Episode
- “Because it didn’t do a million dollars within its first year, I thought that it was just a bad business. I killed it without having the insights that this was actually very successful and you should keep going. So just not having that knowledge and the right expectations hurt that business.” — Ryan Austin, Founder and CEO, Cognota
- “All it takes is when you start missing goals or even if you’re celebrating successes… just means taking a couple days to do that offsite and being brave enough and vulnerable enough as a leadership team to talk about the ugly stuff.” — Ryan Austin, Founder and CEO, Cognota
- “If you want me to trust you and get out of the way, you have to prove and build trust with me.” — Ryan Austin, Founder and CEO, Cognota
- “If it’s not going right, don’t ask me not to get in the weeds because my job is to get in the weeds to make sure that the company is healthy.” — Ryan Austin, Founder and CEO, Cognota
- “If you go and work on anything else outside of those five areas that your CEO stood up, took the time to stand up on stage about, say they’re losing sleep about it and they need your help to accomplish these, and you do anything else with your time or your money than those five things, then you’re failing automatically as a business professional or a business leader.” — Ryan Austin, Founder and CEO, Cognota
Frequently Asked Questions
How do founders know when they are being too impatient with their company’s growth?
Ryan Austin, founder of five companies and CEO of Cognota, argues that most founders apply the wrong benchmark: they compare their trajectory to the rare companies that hit $100 million in under a year. A more accurate standard is Docebo, a learning management system built by a schoolteacher that took ten years to break through $1 million in ARR before achieving meaningful scale. Austin shut down a company generating $10,000 in its first week because it had not reached $1 million in year one — a decision he later identified as the mistake, not the business itself. If your company generates real revenue and real customers, impatience may be the only thing standing between you and success.
What does a productive post-quarter alignment session actually look like for a CEO?
Austin recommends taking two or more days offsite with the full leadership team after each quarter, regardless of whether the quarter was a win or a loss. The goal is to surface what broke, who owns it, and what the team will fix together. The CEO must be willing to take the blame publicly and create enough psychological safety for the leadership team to name the real problems. Austin describes the result as starting the next quarter “fully aligned to execute, focused on the truth.”
How should a CEO manage a new executive hire in the first 90 days?
Ryan Austin, CEO of Cognota, recommends staying present and watching for demonstrated performance before handing off authority — not stepping back simply because the hire was made. Austin attended his new Chief Revenue Officer’s weekly sales meetings until the CRO had shown he could run them without CEO input. Only after that performance was evident did Austin ask the CRO directly whether he should remain on the meeting invite. The CRO said no, and Austin treated that outcome as earned, not given. Austin’s rule for the period before performance is demonstrated is direct: if things are not going right, the CEO’s job is to get in the weeds — because keeping the company healthy is the CEO’s responsibility regardless of who was hired to help.
CEOs Work with Glenn Gow to Scale Their Companies and Careers
Glenn Gow is The Scaling Executive Coach — he coaches ambitious executives into the CEO seat and CEOs into successful exits. With 25 years as a CEO and 5 years in venture capital, Glenn helps leaders scale their companies by scaling themselves first. If this conversation was useful, you can apply for executive coaching with Glenn Gow or apply to be a guest on The Scaling Executive Podcast.
