Notes From a Serial Entrepreneur: 5 Things That Are Easier the Second Time Around

Frank Sinatra, one of my all-time favorites, crooned “love is more comfortable the second time you fall.” When it comes to companies, I definitely agree. Silversheet is my second startup and our goal is to modernize health care administration with products that transform the way healthcare providers and facilities collaborate and connect. I’ve noticed that my love affair with the company is less rocky and that numerous things are significantly easier the second time around. I’m not alone: entrepreneurs who’ve had one successful startup are 12% more likely to succeed in their next venture, compared to first-timers.

Here are five ways I’ve found running a startup is easier the second time around:

  1. Building a technically proficient product
  2. Not only have I learned more about the software development process, it’s also become easier to build products over the past few years. New development platforms have allowed businesses to cut development time by as much as 90%. Even more importantly, I now know how to work with product managers and software engineers. Salespeople and business people tend to think about end goals, and in the case of Silversheet we knew we wanted a product that would streamline physician credentialing.

    I’ve learned that a high-level statement is not a blueprint for building a product. Software products are built to excruciatingly detailed specifications; every single thing that happens must be described precisely: “Turn the handle, pull the doorknob, etc.” When building a product, you need to think about how detailed the process you’re describing actually is.

    Sometimes, businesspeople and software developers end up with mismatched expectations. Businesspeople tend to want programs with lots of features (even if they don’t realize that’s what they’re asking for). As a result, the development project’s scope expands, the costs creep up, and more time goes by. In addition, the most difficult programming problems can’t be solved by throwing money and people at them. You just need time. If you want your software twice as fast, adding two more developers won’t necessarily accomplish this.

    At my first company, EQAL, we initially tried to build something far too complex. I asked for the moon, and our engineering team said “no problem.” Weeks passed, and the login wasn’t even built. This time around, I’ve learned to reign myself in and listen to my product oriented co-founder and engineering team to determine what is actually feasible.

  3. Delegating Business Operations
  4. When you first start managing a company, you quickly learn that management is truly an art and a vocation: there’s a lot that needs your attention, from employment contracts, to accounting, monthly finance meetings, and performance reviews. Some of these operations are pretty boring, but all of them are critical. This time around, I know what I don’t know. I know what’s important and what isn’t. I know what I need to handle myself, and what I can delegate. At EQAL, I would agonize over–and involve myself in–everything.

    The key was not only learning from experience, but educating myself: I talked to friends in business school about what books I should read. I wanted to understand what was involved in each operation, so that I’d know how to evaluate, hire, and manage the professionals across various functional areas. Knowledge gave me the confidence to delegate.

  5. Understanding Hiring Needs
  6. It’s practically a truism that building a successful startup depends on hiring great people. Fortunately, learning to identify talent gets easier with experience, although it’s still challenging. Even the COOs of many Fortune 500 companies spend a significant amount of time on the hiring process, and startups should do the same.

    Experience has helped: it’s taught me how to build an effective screening process–one that makes the sorting easier–and how to describe the job I want someone to do. Having gone through the startup gauntlet, I’m better able to see what the company needs, which makes me much better able to say, “I need someone with these exact skills to play this exact role.” Just being able to get specific helps make this all-important process a little less daunting.

  7. Raising Funds
  8. This one’s simple: Having a track record and a reputation as a successful entrepreneur makes it much easier to raise funds the second time around. Everyone wants to bet on a winning horse, and growing a company from an idea to a successful exit demonstrates tenacity and business acumen. Success begets success.

  9. Planning for the Future
  10. Every business needs to set milestones to plot out its growth. This presents unique challenges at a startup because the landscape is always changing, but, the simple act of going through the process once–taking the steps to chart your company’s course–makes it much easier to navigate on your second voyage.

At the same time, it’s worth remembering, that it’s one thing to write down your goals on a piece of paper and quite another to get your team galvanized and motivated enough to achieve them. As one of my EQAL investors, Ben Horowitz explained in TechCrunch, you’ve got to manage not just your people, but yourself. If you do, you’ll no doubt be able to make your second love even sweeter than your first one.

Miles Beckett, M.D. is CEO Co-founder of Silversheet, a company dedicated to developing software solutions that transform the way healthcare facilities and providers collaborate and connect.

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