What would you do different if your startup was launching today?


With some new opportunities in front of me, I been pondering what I'd do differently from my last startup a little over 12 years ago.

If you've founded a successful business, what would you do more of and what would you do less of if you had a chance to lead another startup today?


asked Mar 7 '10 at 06:09
Keith De Long
5,091 points
  • I've been surprised at my leading observations: 1. I'd focus much more rigorously on the bottom line. For too long I led with a romantic notion of entrepreneurship. Profitability brings stability, resources, and opportunities. I didn't get that clearly in the early years of my startup. 2. I'd do a much better job balancing my personal well being with work. As I wrap up my forties I am painfully aware that I am not immortal. The decades of neglecting my health for the sake of work has extracted a cost that did not need to be paid. – Keith De Long 14 years ago

4 Answers


For some strange reason, it's easier to see what you did wrong last time round than what you did right. I'm sure me and my team must have done a few things right as we ended up being acquired (to use Dharmesh's term, in a modest liquidity event), but I'm painfully aware of the things we did wrong:

  1. Along the lines of Jarie's point about innovation - recognise that you are small start-up, not Microsoft or Oracle. In trying to build our first trading system product, we attempted to build our own messaging middleware and our own equivalent of WPF, complete with data binding and dynamic user interfaces.

    The fact that Microsoft produced such a thing a few years later meant that maybe we had great vision and insight, but trying to do in a team of three devs was just plain stupid. So the lesson there is avoid over-engineering.

  2. Along the lines of Chris's point about focus and Jarie's point about distractions - having razor focus is massively important. In one sense, it matters less whether you're on the right track in terms of whatever area you go after than it does that you go after it with everything.

    In the seven years between incorporation and acquisition we took on tons of consulting work just to pay the bills, much of it unrelated to our product. In the early stages if you're self-funded, this is almost inevitable, but once you have a product, then you should make sure that any other work you do supports your product strategy.

  3. Following on from the last point, second time around I would avoid growing staff at the same rate as income. We did this because we wanted to be able to produce more product, but it was self-defeating because we ended up taking on non-core work to support our high outgoings. Put another way, keep some money in the bank for a rainy day or two.
  4. Finally (although I'm sure we made plenty of other mistakes), I would say that when it is time to employee a sales/marketing person (i.e., once your product is half-decent), then understand that they are very different animals than developers. Sales people work differently (especially in the enterprise space - they always seem to be socialising at lunch or dinner, when the devs are slaving over a hot compiler) - so a different management approach is needed, and they need to be properly supported by the rest of the business.

    By this I mean that, for example, when they come with a feature request for a specific client in order to clinch a deal, then it's good if the business has the capacity to digest and deliver that - we were always flat out working on the the next big thing that our sales guy always had to make do with what he had. (I'm not saying throw your product management process to the wind, but just try and be a bit flexible in support of the sales process).

Interesting your comment about founder health - there is something recent on this subject on Jason's blog I believe - I wonder if we are coming into a new generation of entrepreneurs where maintaining one's health is seen as a fundamental pillar of successful leadership. I certainly didn't do myself any favours first time round and have got quite some catching up to do before I turn fifty :-).

answered Mar 8 '10 at 00:38
Steve Wilkinson
2,744 points
  • Some good insights Steve, Thanks. Over engineering and focus are good things to think about together. I've resisted the articles and discussions about releasing 'good enough' software, but there is truth in these types of articles. Pursuing 'good, but not everything I wish it was' is a great engineering standard with iterative products like software. – Keith De Long 14 years ago


Several things come to mind:

  • Focus on getting quick to profit: The faster you turn a profit, the better because that means you need less investment.
  • Minimize distractions: The more markets and products you go after, the more money you will burn through. Pick a path and drive it hard. If it's the wrong path, then kill it and move on.
  • Take as little investment as you can: Investors are great but the amount of money you take from them as strings. They want a return and that return might not be in the best interest of the company.
  • Don't do too innovative a product: Innovation is great but doing too much will sap your resources and delay getting to market. I know this is a sad statement but it can be really frustrating solving tons of new problems and delaying your launch.
answered Mar 7 '10 at 13:07
Jarie Bolander
11,421 points
  • +1 for Focus. It should have been on my list as well! – Keith De Long 14 years ago
  • On the advice of an older, wiser friend, I've stayed away from the temptation of outside investors all together. Looking back, it's some of the best advice I ever received as an entrepreneur. – Keith De Long 14 years ago


This thread is in a similar vein:

http://www.brightjourney.com/q/entrepreneurs-3-best-pearls-wisdom-received-startup-ventures To me what I learned is to focus on the product and demand. Anything else should be minimized. Ultimately how are you going to drive the revenue. And how are you going to get the product to be what it needs to be to make it marketable and sellable. Questioning everything I do and figuring out how it ties back into one of those two things.

As a marketer at one startup long ago I got caught up in the brand and logo and and this and that, losing sight of the need to get money in the door. Now I am a huge brand advocate and believe it's a part of the equation. But as a foundation, how are you going to make the money.

answered Mar 7 '10 at 06:24
4,214 points
  • While the thread you mention is is similar (and a good link), it's focus is on what others have taught you as opposed to what you've learned through experience in a startup. I appreciate your personal contribution to the discussion. – Keith De Long 14 years ago


My answer is based upon my current company, which is a very low-tech, locally-focused healthcare services company. In that context, at least, I would do these things differently if I were starting it over again:

1) Hire a great salesperson ("great" depends on a lot of factors, which would be different from one case to the next) from the beginning.

2) Focus on profitability. "Happiness is positive cash flow, all else will come later".

3) Build a well-grounded strategic plan, and track your performance against it often, adjusting course as needed and paying CLOSE attention to the details. Be very honest with yourself about where you are succeeding and where you are not.

4) Hire slowly and carefully. Fire quickly when realize that you've made a mistake in hiring. Get it over with and move on.

answered Mar 14 '10 at 00:15
433 points
  • +1 for the "Fire quickly" addendum - it is critical to cut your losses quickly, whether they are in time/effort/direction or in terms of mismatched employees. The cost of hiring/rehiring is not trivial, but the cost (both monetary and intangible) of sustaining an employee who doesn't share your vision and values is much more! – Seenu 14 years ago

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