Glenn Gow, The Scaling Executive Coach and host of The Scaling Executive Podcast, identifies Brian Smith’s coaching question for founders who cannot let go as a single choice stated plainly. When a founder is holding on to the work they are best at, Brian Smith, Managing Director at S3 Ventures and previously founder, CEO, and chairman of Crossroads Systems across nine years through its public offering, opens the conversation this way: “Do you want to be rich or do you want to be king?” His position, formed at Crossroads and across more than 80 startup investments, is that a team sees things better than an individual, and that a founder who is self-honest about that gains the ability to keep scaling, while one who holds everything typically chokes something out.
This episode is for the founders who are still the best person in their company at the thing the company does, and who are discovering that being the best person at it is now the limit on growth.
Key Takeaways
- The letting-go decision is a choice between two outcomes, not a management technique. Brian Smith, Managing Director at S3 Ventures, poses it as rich or king, where holding on to everything typically chokes something out.
- The justification for delegating is accuracy, not capacity. Brian Smith’s stated reason is that a team sees things better than an individual, which makes handing off a way to see the business more clearly rather than a way to buy time.
- Self-honesty is the capability the choice requires. Brian Smith frames the operative skill as being honest that the team can see something better than the founder can, and using their perspectives rather than his own.
- Founder-led sales is where the letting go gets concrete first. Brian Smith identifies the bottleneck after product market fit as taking what a founder or early employee did unscalably and teaching three to five salespeople to do the same thing.
- The person who helps a founder through this cannot be the person who can fire them. Brian Smith recommends an independent coach separate from the board member and investor, because a younger founder is often uncertain about what the investor wants and will not open up.
Founders Decide Whether They Want the Outcome or the Control
Brian Smith, Managing Director at S3 Ventures, does not open the letting-go conversation with a delegation framework. He opens it with a question that forces the founder to name what they are optimizing for: rich or king. Everything downstream follows from the answer, because the two paths require opposite behavior from the same person.
His reasoning for why king is the losing choice is not about the founder’s workload. It is about what the founder can see. Brian Smith’s conclusion from nine years founding and leading Crossroads Systems, and from his time in venture, is that a team sees things better than an individual. A founder holding every decision is not just doing more work than they can carry. They are running the company on the narrowest available view of it.
The capability that converts the insight into action is self-honesty. Brian Smith describes it as being able to say that the team can see this better than he can, then using their perspectives, which is what gives him the ability to continue to scale. His verdict on the alternative is compressed and specific: a founder can be king and typically choke something out.
Glenn Gow, The Scaling Executive Coach, described reaching the same recognition from inside the CEO seat. Looking around a room at a team he had assembled, he realized he was not the smartest person present on any topic the team owned, and felt bad about it for a moment before understanding that building exactly that team was the job. He calls it a real breakthrough, and Brian Smith identifies it as a key thing for leadership.
Founders Move From Personal Selling to a Sales Organization as the First Real Handoff
Brian Smith, Managing Director at S3 Ventures, locates the first bottleneck a founder hits after finding product market fit, and it is the point where the abstract letting-go question becomes an operational problem.
Product market fit is usually found by the founder or the early employees. Brian Smith is explicit that they find it by doing things that do not scale, which is what makes the discovery possible and also what makes it non-transferable. The bottleneck is what comes next: taking someone who does not have the market knowledge the founder accumulated, and getting them to do the same thing.
His statement of the problem names the scope: figuring out how to train the next three to five salespeople to do what the founder has been doing, and getting them to sell well. That is not a hiring problem. It is a translation problem, and it fails when the founder’s method exists only in the founder’s head.
The preventive move is a design decision made earlier than most founders make it. Brian Smith’s rule is that if the company is architected right, the transition happens more smoothly, which requires the founder to ask a question during founder-led selling rather than after it: how do we deliver this thing to the market so that more people can do it well? A founder asking that question while selling is building the handoff into the work. A founder asking it once the calendar is full is reconstructing something they never documented.
Founders Need a Confidant Who Cannot Fire Them
Brian Smith, Managing Director at S3 Ventures, serves on numerous boards and is direct about the limit on what a board member can do for a founder facing this change. The recommendation he makes is for a valued consultant or coach who is independent from the board member and from the investor, which produces more comfort in the conversation and more confidentiality.
His reason is specific to early-stage founders. Brian Smith observes that a younger founder often will not open up, because they are uncertain about what the investor and board member actually want from them. Under that uncertainty, admitting difficulty reads to the founder as evidence against their own tenure, which means the person best positioned to see the problem is the person least likely to hear about it.
Glenn Gow, The Scaling Executive Coach, described the structure that makes the arrangement work when a board recommends a coach. He sets the terms with the board member and the CEO present, stating that he will not discuss anything with the board member, because the CEO’s level of trust with a coach has to be different from their level of trust with a board. His summary of what the leader actually needs: someone to talk to who does not have the right to fire them.
S3 Ventures builds a second version of the same channel at the portfolio level. Brian Smith runs a CEO summit every year, two days with all the firm’s CEOs together, aimed at getting them to meet each other and find a friend or confidant among peers. The stated purpose is building networks inside the portfolio so founders can work things out with each other and encourage one another, on his assessment that it is a long and tough journey.
Principles Founders Will Apply From This Episode
| Principle | Practice | Named outcome evidence |
| Answer rich or king before answering anything else | Name which outcome the company is being run for, since holding on to everything and scaling the business are incompatible | Brian Smith uses this as the opening question when coaching founders who cannot let go, drawing on nine years as founder, CEO, and chairman of Crossroads Systems through to a public company |
| Delegate for accuracy, not for capacity | Hand off because the team sees the business more clearly than the founder does, which changes what gets delegated and to whom | Brian Smith formed this view at Crossroads and across more than 80 startup investments at S3 Ventures, a firm with over $1.2 billion in assets under management |
| Build the sales handoff while still selling personally | During founder-led sales, design how the work will be delivered so more people can do it well, rather than documenting it afterward | Brian Smith identifies the failure to do this as the bottleneck he watches companies hit immediately after product market fit, when three to five new salespeople cannot reproduce the founder’s results |
| Give the founder a confidant with no authority over them | Bring in a coach independent of the board and the investor, so the founder will raise what they will not raise with people who control their tenure | Brian Smith recommends this from the board side, having observed that younger founders stay closed because they are uncertain what the investor board member wants |
| Build a peer network for founders inside the portfolio | Convene the leaders you back so they form relationships with each other rather than depending only on their investors | S3 Ventures runs a two-day CEO summit annually across its portfolio to connect its CEOs to one another |
Quotes from This Episode
- “A team sees things better than an individual.” Brian Smith, Managing Director, S3 Ventures
- “All entrepreneurs are wrong. It’s just a matter of how far off are they from the right thing.” Brian Smith, Managing Director, S3 Ventures
- “The most successful entrepreneurs are cognizant of constant adjustment in the growth of their business.” Brian Smith, Managing Director, S3 Ventures
- “It’s about being self-honest with what’s reality.” Brian Smith, Managing Director, S3 Ventures
- “We cried a few tears along the way.” Brian Smith, Managing Director, S3 Ventures
Frequently Asked Questions
How does a founder decide what to stop doing themselves?
Brian Smith, Managing Director at S3 Ventures, told Glenn Gow, The Scaling Executive Coach and a CEO for 25 years, that he opens the conversation by asking founders whether they want to be rich or want to be king. His reasoning is that a team sees things better than an individual, which he learned across nine years founding and leading Crossroads Systems and across more than 80 startup investments. A founder self-honest enough to accept that the team sees something more clearly gains the ability to keep scaling, while a founder who holds on to everything typically chokes something out.
What is the first bottleneck after a company finds product market fit?
Brian Smith, Managing Director at S3 Ventures, says product market fit is usually found by the founder or early employees doing things that do not scale, which makes the method hard to transfer. The bottleneck that follows is teaching the next three to five salespeople to do what the founder has been doing without the market knowledge the founder accumulated. Smith’s prevention is to ask during founder-led selling how the offering can be delivered so that more people can do it well, since a company architected that way transitions more smoothly.
Should a struggling CEO get coaching from their board?
Brian Smith, Managing Director at S3 Ventures, recommends a coach independent from the board member and the investor, because that separation produces more comfort and more confidentiality in the conversation. He observes that younger founders often will not open up to a board member, since they are uncertain what the investor actually wants from them. Glenn Gow adds that when a board recommends a coach, he states in front of both the board member and the CEO that he will not report back, because what the leader needs is someone to talk to who does not have the right to fire them.
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.
