It doesn’t make sense to teach about startups and entrepreneurship if you’re also not in the pool swimming at the same time. Since I did my first startup many years ago at age 40, I’ve never lost the bug. But now, instead of actually having to live the pain and agony every day, I try to support young entrepreneurs by my role as a coach, advisor, board member, and mentor. There probably isn’t anything I haven’t seen yet (and I can tell you, I’ve seen some pretty strange things) that I can’t help a start up with – or find someone who can.

Leadership development

No company grows without significant people issues. Are you delaying crucial human resources decisions? People don’t always grow at the same rate as their company; typically, less than 25% of a company’s initial leadership is able to transition through its growth stages.

The manner in which you handle these issues is the single most critical factor in success vs. failure. Delayed “people” decisions equal delayed success.

  • How do you ease out or transition the old team?
  • How do you find and integrate the new lead players you need?
  • How do you identify when management and communication skills become as important as technical abilities?
  • How do you build a team that can perform at the level you need to succeed?


Too many startups suffer from the “strategy of the month” and the “project du jour” syndrome.

  • Is the issue at hand building more product or better product?
  • Should you choose a vertical market?
  • If so, what opportunities do you walk away from?
  • Why does everyone keep telling you to focus? Don’t they understand that you need to be nimble and adaptable

Scaling and finance

Whether you’re backed by venture capital or self-financed, the issues are the same. You want to grow fast; your opportunity and your market demand this. But financing your growth is more than just finding a source of capital. It’s having a funding strategy and knowing if you’re ready.

  • Do you need outside financing now?
  • How much capital do you need? Can it be financed in stages?
  • What form/source of capital is most appropriate for your business?
  • Are you ready to seek financing?
  • Is your business model (and plan) well-defined and clearly stated?
  • Can you articulate your market and sales strategy?
  • Have you prepared the necessary materials to cut through the clutter?
  • What are your valuation expectations? Are they realistic?

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