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People Management: Startup Teams Should Dip but not Skip

Both Sides of the Table

You’ll get sales information from your VP of Sales, marketing information from your VP Marketing, tech information from your CTO and so on. By going on sales calls you pick up directly the feedback of what customers want and also what they’re telling you about competition. Skipping is insidious.

Startup 308
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Announcing a Deal I’ve Wanted to Talk About for a Year

Both Sides of the Table

I acted as the occasional mentor, advisor and coach to Ethan. And because I wanted Ethan to be able to attract a great team, build & iterate a product, test it with initial customers and refine his strategy before having to take the wrappers off of his company. The company was called Red Beacon. So there you have it.

CTO Coach 359
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Venture Capital is About Human Capital

Both Sides of the Table

We help founders through difficult moments, we help coach, we act as sparring partners, we help them resolve conflicts when they’re fighting with co-founders and we help them deal with adversity as well as successes. That’s why I often say The role of VC is “chief psychologist.”

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Be Careful About Being a Meddling Startup CEO

Both Sides of the Table

In practice it can be a fine line between sparring partner / coach and stepping over the line to brute-force persuasion. So he would allocate say – 20% to sales, 15% to marketing, 20% to eng priorities, 10% to customer support, 10% to ops, 20% to ‘platinum customers’ and maybe 5% directly to me as the CEO.

Startup 150
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What Makes an Entrepreneur? Four Letters: JFDI

Both Sides of the Table

You’re sales person is getting blocked by the CTO who says she shouldn’t go above him but the CTO isn’t approving the deal. Yes, I know it’s my job as the CEO to be the coach for people and that’s fine. Should she take a chance and potentially ruffle feathers? I was a bull in a china shop.

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8 Tips To Get the Most Out of Your Investors and Board

Both Sides of the Table

But the thing I am most proud of about Rob is that he has taken a company with a uniquely talented founder & CTO – Nick Halstead – and managed to build a very tight working relationship with Nick where we drive world-class product development without having the usual founder / CEO conflicts. Ask for short conference calls.

Tips 365
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Technology Roles in Startups

SoCal CTO

I’ve worked with 30+ early-stage companies in all sorts of capacities (and spoken to many, many more), so I thought it might be worthwhile trying to classify the various ways that I’ve engaged in different technology roles in startups. Actually, David’s taking even broader roles than I generally do as he’s CEO for at least one startup.