Glenn Gow, The Scaling Executive Coach and host of The Scaling Executive Podcast, identifies Dan Corrigan’s single largest scaling regret as a timing error rather than a judgment error. When a bootstrapped company is growing and every dollar is committed to inventory, Dan Corrigan, co-founder and CEO of Organic 3 and the sole authorized American distributor for Rosita Real Foods since 2014, holds that the founder will hire sooner than the cash flow appears to allow, because the alternative is what happened to him: waiting until he had to cry uncle, by which point he describes himself as on the burnout train. Dan Corrigan launched Corganic in 2007, co-founded Organic 3 in 2009, and now sells into more than twenty countries.
This episode is for the bootstrapped founders whose revenue is climbing, whose cash is tied up in inventory, and who keep concluding that this quarter is not yet the quarter to add a person.
Key Takeaways
- The hiring delay is a cash flow trap, not a discipline problem. Dan Corrigan, co-founder and CEO of Organic 3, describes producing supplements as laying out cash upfront, leaving inventory on the shelf and nothing in the bank, so that growing sales and growing expenses arrive together.
- The wrong trigger for hiring is the founder’s breaking point. Dan Corrigan waited until he could not continue, and names hiring sooner and earlier as what he would change if he did it again.
- Enjoying a task is not a reason to keep it. Dan Corrigan’s guiding phrase is who not how, and he applies it even to work he likes doing, on the basis that someone else will thrive in that position.
- Coaching showed him what his own value to the company actually was. Dan Corrigan entered coaching believing it was not for him, and describes what it produced as a view of the big picture and of where his contribution sat.
- Delegation only holds where mistakes are permitted. Organic 3 runs on a core value of know better, do better, and Dan Corrigan reports employees telling him the company means what it puts on the wall.
Founders Hire Before the Cash Flow Math Feels Safe
Dan Corrigan, co-founder and CEO of Organic 3, describes the specific squeeze that keeps bootstrapped founders from hiring, and it is not caution. Producing supplements means laying out cash before any revenue arrives. The company then holds inventory with little in the bank. Sales grow, which requires buying more product, which consumes the cash the sales produced. Dan Corrigan calls it a catch-22: sales are growing and expenses are growing with them.
Inside that squeeze, a hire looks like the one discretionary expense on the list. Every other outflow is attached to product the company has already committed to. That is why the question Dan Corrigan describes wrestling with is when the right time to hire actually is, and why the answer kept moving.
What he actually did is the warning. Dan Corrigan waited until he had to cry uncle, until he could not do it anymore, and describes himself at that point as burnt out. His correction, stated as the thing that would have saved him the most time and effort, is that he would have brought people on sooner.
The reason earlier is better is that a hire made at the breaking point arrives with the founder already depleted, which is the worst condition in which to onboard, train, and hand off work. Glenn Gow, The Scaling Executive Coach, frames the objective a founder is buying with that hire: past the earliest scrappy days, the CEO’s primary job is building a leadership team, because that team is where the leverage comes from.
Founders Ask Who Rather Than How, Including for Work They Enjoy
Dan Corrigan, co-founder and CEO of Organic 3, encountered the framing that changed his hiring while he was still early in bringing people on, and it stuck because it removed the question he had been asking himself. The phrase is who not how: rather than working out how to do something, find the person who can do it.
The part of his application that goes further than most is the qualifier he attaches. Dan Corrigan’s rule covers things he is not very good at, and then extends past them: even if he likes doing the work, his conclusion is to get out of the way and put somebody in that position who will thrive in it.
That distinction matters because enjoyment is the most common reason founders keep work they should have handed off. A task the founder dislikes gets delegated at the first opportunity. A task the founder enjoys and is mediocre at can survive for years, defended on the grounds that it keeps them close to the business.
The test Dan Corrigan applies replaces the founder’s preference with the outcome for the company: not whether he wants the work, but whether someone else will do it better. That is also the honest version of the hiring question from the previous section, since the roles worth opening first are the ones where somebody else clears the bar the founder never will.
Coaching and Peer Groups Show a Founder Where Their Actual Value Sits
Dan Corrigan, co-founder and CEO of Organic 3, started where most bootstrapped founders start on this question. His description of the mindset is that a gritty bootstrapped entrepreneur believes they can do it all, which made coaching read to him as something for other people.
What changed his position was the content rather than the format. Dan Corrigan describes coaching as letting him see what his value to the company was, and what his team was not doing, which he sums up as looking at the big picture. That is the diagnostic a founder cannot run alone, because the founder is the one variable they cannot observe from outside.
Organic 3 has since invested in coaches for Dan Corrigan and for other people on the team, and he has joined peer groups including a visionary group where leaders discuss struggles in their own businesses. His stated reason those groups pay off is transferability: the problems belong to different companies, and enough of the material carries across.
Glenn Gow, The Scaling Executive Coach, brought his own record to the same point, noting that he worked with a coach for seventeen years while serving as a CEO for twenty-five, and understood from that experience how valuable it was to his own growth.
Delegation Holds Only Where the Company Permits Mistakes
Dan Corrigan, co-founder and CEO of Organic 3, built the condition that makes handing off work survivable, and it is a culture rule rather than a management technique. One of the company’s core values is know better, do better, which he uses to establish that making mistakes is normal and common and is how the company grows.
The evidence that it operates rather than decorates comes from the people subject to it. Dan Corrigan reports employees telling him after joining that the company actually means what it says about culture and core values, rather than printing them and putting them on the wall, and that people are given considerable leeway.
His own behavior is the enforcement. Dan Corrigan has been asked by his team why he does not get upset and yell, and his answer is a claim about returns: allowing people to be accountable for themselves pays far more dividends than correcting them or showing disdain.
Glenn Gow, The Scaling Executive Coach, states the harder version of the same standard, which is that a leader should reward someone for a mistake that was not catastrophic, acknowledging that they gave it their best and did the right things even though it did not work out. He notes that some leaders find this difficult. The connection to hiring is direct: a founder who hands off work and then punishes the first error has not delegated anything, because the person will route every decision back to the founder rather than risk being wrong.
Principles Founders Will Apply From This Episode
| Principle | Practice | Named outcome evidence |
| Hire before the founder breaks | Treat the hiring decision as a growth requirement rather than a discretionary expense, and act ahead of the point where the work becomes unbearable | Dan Corrigan waited until he could no longer continue, reached burnout, and names hiring sooner as the change that would have saved him the most time and effort while building Organic 3 |
| Ask who, not how, even for work you like | Screen tasks on whether someone else will thrive in the role rather than on whether the founder enjoys it | Dan Corrigan adopted this framing early in his hiring at Organic 3, which now supplies Smidge Small Batch Supplements and Rosita Real Foods into more than twenty countries |
| Buy an outside view of your own contribution | Use coaches and peer groups to see what only the company’s leader cannot observe, then act on the gap | Dan Corrigan moved from believing coaching was not for him to investing in coaches for himself and his team, and joining a visionary peer group |
| Make permitted mistakes an operating value | State the standard, then demonstrate it by not correcting or punishing errors that came from good effort | Organic 3’s know better, do better value is what employees cite when they tell Dan Corrigan the company means what it puts on the wall |
| Grit is a business skill before it is a story | Acknowledge errors, decline to dwell on them, and return to solving the problem | Dan Corrigan carried this from a decade recovering from a severe intestinal condition into building Corganic in 2007 and Organic 3 in 2009, and into a Rosita distribution agreement that took time to gain traction |
Quotes from This Episode
- “When you start off as a bootstrapped, gritty entrepreneur, you think you can do it all.” Dan Corrigan, Co-Founder and CEO, Organic 3
- “I was kinda on the … burnout train.” Dan Corrigan, Co-Founder and CEO, Organic 3
- “The only thing that matters is how you … acknowledge them and move on.” Dan Corrigan, Co-Founder and CEO, Organic 3
- “Anytime you have a … good, real tight personal relationship, then when you hit bumps on the road, then both sides can really accommodate each other.” Dan Corrigan, Co-Founder and CEO, Organic 3
- “The goal is to empower people.” Dan Corrigan, Co-Founder and CEO, Organic 3
Frequently Asked Questions
When should a bootstrapped founder make the first hire?
Dan Corrigan, co-founder and CEO of Organic 3, told Glenn Gow, The Scaling Executive Coach and a CEO for 25 years, that he waited until he could no longer keep going and reached burnout, and that hiring sooner and earlier is the change that would have saved him the most time and effort. The trap he describes is structural: producing supplements means laying out cash before revenue arrives, leaving inventory on the shelf and little in the bank, so growing sales and growing expenses arrive together and the hire looks like the only discretionary expense. Glenn Gow’s framing is that past the earliest scrappy days, a CEO’s primary job is building the leadership team that provides leverage.
How does a founder decide which work to hand off?
Dan Corrigan, co-founder and CEO of Organic 3, applies a phrase he encountered early in his hiring: who not how, meaning find the person who can do the thing rather than working out how to do it yourself. His version extends past work he is not good at to work he actively enjoys, on the reasoning that he should get out of the way and put someone in that position who will thrive there. That test replaces the founder’s preference with the outcome for the company, which is why it catches the tasks a founder would otherwise defend keeping.
What does a CEO get from coaching or a peer group?
Dan Corrigan, co-founder and CEO of Organic 3, began by thinking coaching was not for him, on the bootstrapped founder’s assumption that he could do everything himself. What it gave him was a view of what his own value to the company was and what his team was not doing, which is the assessment a leader cannot run on themselves. He has since invested in coaches for himself and other people at Organic 3, and joined a visionary peer group where the struggles belong to other businesses but enough of the material transfers.
Founders Work With Glenn Gow to Scale Their Companies and Their Own Capability
Glenn Gow is The Scaling Executive Coach. He coaches ambitious executives into the CEO seat and CEOs into successful exits, drawing on 25 years as a CEO and 5 years in venture capital. 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.
