Advice for Budding Entrepreneurs

The following words* were written by Paul Graham (successful venture capitalist, computer programmer, and essayist – how’s that for a combo!) on the qualities needed to be a successful startup entrepreneur:

Be relentlessly resourceful.

Not merely relentless. That’s not enough to make things go your way except in a few mostly uninteresting domains. In any interesting domain, the difficulties will be novel. Which means you can’t simply plow through them, because you don’t know initially how hard they are; you don’t know whether you’re about to plow through a block of foam or granite. So you have to be resourceful. You have to keep trying new things.

That sounds right, but is it simply a description of how to be successful in general? I don’t think so. This isn’t the recipe for success in writing or painting, for example. In that kind of work the recipe is more to be actively curious. Resourceful implies the obstacles are external, which they generally are in startups. But in writing and painting they’re mostly internal; the obstacle is your own obtuseness.

There probably are other fields where “relentlessly resourceful” is the recipe for success. But though other fields may share it, I think this is the best short description we’ll find of what makes a good startup founder. I doubt it could be made more precise.

Now that we know what we’re looking for, that leads to other questions. For example, can this quality be taught? After four years of trying to teach it to people, I’d say that yes, surprisingly often it can. Not to everyone, but to many people. Some people are just constitutionally passive, but others have a latent ability to be relentlessly resourceful that only needs to be brought out.

This is particularly true of young people who have till now always been under the thumb of some kind of authority. Being relentlessly resourceful is definitely not the recipe for success in big companies, or in most schools. I don’t even want to think what the recipe is in big companies, but it is certainly longer and messier, involving some combination of resourcefulness, obedience, and building alliances.

This test is also useful to individuals. If you want to know whether you’re the right sort of person to start a startup, ask yourself whether you’re relentlessly resourceful. And if you want to know whether to recruit someone as a cofounder, ask if they are.

You can even use it tactically.

If I were running a startup, this would be the phrase I’d tape to the mirror. “Make something people want” is the destination, but “Be relentlessly resourceful” is how you get there.

“Relentless” has a lot of negative connotations: unyielding severe, strict, harsh, never resting. But it’s really just further along the spectrum of what I call “showing up,” doing things to consistently move the ball ahead (whichever ball you’re moving). If you’re looking to break new ground you should evaluate where on the “doing” spectrum you want to be, and then ask if that is far enough towards where you need to be to successfully accomplish your goal.

“Resourcefulness” is a fascinating quality, a cross between creativity and cleverness. It’s an ability to find new resources to address a problem. People who are “stuck” in their careers / lives typically consider themselves to be anything but resourceful. They’ve tried and tried, but have run out of ideas. That’s why so many of the people sitting in my office have come to me, often hesitantly because they feel they shouldn’t need “outside help,” but of course the very act of searching for outside help is a form of resourcefulness.

Your #1 destination for resourcefulness should be Google. Whatever problem or issue you are facing, you can be pretty sure that someone else (or maybe even hundreds or thousands of others) have also faced it, have valuable perspective to share, and have taken the time and effort to express that perspective so that it can benefit others. I am amazed at how many of my clients say “Good idea!” when I suggest that they consult Google. Make it your default setting whenever you feel unsure or stuck – enlist those outside resources!

If you’re exploring a career change, here’s Jim’s 4-stage process

01

Develop Your Profile

Jim helps you build a concise narrative capturing everything relevant: who you are, what drives you, and where you want to go.

  • Professional history, key experiences, defining traits
  • Core strengths and preferred work environments
  • Salary range, location, company size, and your real decision criteria
  • Your values
02

Identify Promising Options

Jim identifies paths with clarity including responsibilities, entry points, challenges, and genuine trade-offs.

  • Compensation outlook and growth trajectory
  • Transition pathways and entry requirements
  • Key advantages and honest trade-offs of each path
03

Evaluate and Prioritize

Jim assesses each path against your strengths and constraints. A prioritized shortlist formed based on logic and AI feedback.

  • Alignment with strengths, interests, and real constraints
  • Comparison across fit, feasibility, and long-term upside
  • A focused finalist list for real-world validation
  • Conversations with people doing the actual work being considered
  • Research and AI provide validation of choices
04

Getting the Job

Jim ensures that your networking outreach, resume, LinkedIn profile, elevator speech, and interview performance are superior.

  • Network outreach and targeted introductions
  • Independent research and industry trend analysis
  • Informational conversations with people in those roles
01
Jim helps you build a concise narrative capturing everything relevant: who you are, what drives you, and where you want to go.

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Working with Jim was a refreshing and positive experience. As a first-timer to working with a coach, I wasn’t sure what to expect. Jim was spot-on in identifying the primary goals and we achieved them within the four weeks he had predicted. His great demeanor made the process effective and easy. Jim is truly delighted in the progress his clients make. This became clear when seeing the broad smile and satisfaction on his face when he realized we achieved our stated goals and that I had the tools to take the next step in my professional and personal success. He’s a great resource to have.

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I am so incredibly grateful for Jim’s guidance during a challenging career change. His insight, feedback, and support were essential to my success in landing a dream job. From helping me chart a new course and finding a new passion after burning out in a draining career, to coaching me through final interviews, he was with me every step of the way. I cannot recommend him enough!

Caitlin Lochridge

As an executive search/headhunter I have been lucky enough to partner with Jim on a number of occasions. I have referred several local and remote (Skype, etc.) mid-level to executive-level candidates to him who have reported back to me with rave reviews. Jim has also consulted with me whenever my executive search expertise has been a helpful element to his full-service thoughtful career advice he provides his clients. 100% class act and worth the investment.

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Jim Weinstein
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