As for your point about golden handcuffs, that's definitely an issue. It's a lot easier to risk everything when everything is an old car and a little furniture.
I like your point about not going it alone, but how does someone with little experience decide whom to lean on? When I was 25 I would have had no clue how to evaluate the skills, experience, and suitability of a partner or of people to fill leadership roles...
Dave: Nice points. Agreed that if you work for a startup, you're not necessarily going to learn from the best--and note to self; stop having employees pick up my tuxedos. (Kidding.)
In that regard, I would strongly support a young or first-time entrepreneur working for a VC-funded start-up. Most VCs are very good about only investing in start-ups with great founders and solid management teams. Clearly bigger companies generally have better managers than start-ups, but the VC-backed start-up is unique, so I like that option a lot: You learn from great people, wear many hats, and learn about the start-up environment.
Case in point: All three of YouTube's founders had previously worked at PayPal when it was a start-up.
With regards to how someone with little experience can decide who to lean on, this is the same hiring challenge that business owners and/or managers face (even though they might have more experience under the belts). My two biggest tips in this regard are as follows: First, rely on referrals. Tap whatever network you have (friends, family members, professors, etc.) and ask who they know who might be a great fit. This is the best way to find reliable people.
Secondly, look at each candidate's prior results in detail. It doesn't matter that they have a fancy education or gained employment at good firms in the past. What they accomplished at those past firms is what's important. Make sure they have a track record of achieving great results, including always checking their references.
Getting Sales Experience
Jeff: Can't argue. Since you're on a roll, how does a would-be entrepreneur gain a skill like sales skills?
That's definitely a downside to working for a big company. When I was in manufacturing, sales seemed to happen by magic. Work just showed up and we ran it. In fact, we used to complain about salespeople not selling the "right" kind of work. We only cared about productivity--since that's how we were measured--and not profitability, so we hated any jobs that made us less productive.
Dave: Teaching sales skills is often challenging. However, I think that if you are passionate about anything, you generally can harness good sales skills.
Like my kids; they have no formal sales training, but if we drive by an ice cream store and they really want ice cream they'll give me a pretty compelling sales pitch as to why I should stop.
So I think that entrepreneurs who are passionate about their company will have some innate sales skills when it comes to selling their company and products/services to advisors, employees, customers, investors, etc. However, like other skills, sales skills must be honed and improved. Fortunately there are lots of sales training programs out there, that, when combined with actual day-to-day selling can greatly improve sales ability. Plus I revert back to getting advisors and/or hiring employees with great sales skills; the more you can interact with and learn from great sales people, the more you will learn this important skill.
Final Words of Advice
Jeff: So looking back, what would you have done differently?
In my case I definitely worked for a big company for too long. I can argue that every year I learned a little more, but after a while what I gained was incremental compared to the first years. Since I started so low on the totem pole--any lower and I would have been underground--it took years for me to get promoted into positions where I learned a lot that helped me later... but even so I would have left years sooner than I did.
And more importantly I would have always had a plan in mind: For too long my plan was only how I could be a better employee... not how I could be a better employee and prepare myself for someday starting my own business.
Dave: Done differently, I would have started my career at a VC-backed start-up (it would have been nice to know what "venture capital" even was back then). I think I would have learned a ton, and within one year, I would have gotten great experience and gained a good sense as to whether the start-up was poised for success.
If so, I may have stayed longer. If not, I might have joined another VC-backed start-up and gained great experience there.
If I felt my business idea at the time was both fantastic and time-specific (i.e. the window of opportunity to launch it was fairly small) then I would have entertained the option of starting my own venture from the get-go.
If I did that, (with my knowledge now) I would have found and surrounded myself with great advisors--other entrepreneurs who have "been there, done that" and could have helped guide and educate me as I embarked on an entrepreneurial endeavor... which no doubt would have presented me with numerous obstacles that I otherwise would have been ill-prepared to face.
