What I’ve learned in 20+ years of building startups

What I've learned in 20+ years of building startups.

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What I’ve learned in 20+ years of building startups…

In the fast-paced world of startups, two decades of experience can teach you invaluable lessons. From the trenches of entrepreneurial ventures, here are the distilled wisdom and key takeaways from a seasoned startup veteran’s 20-plus-year journey.

What I've learned in 20+ years of building startups
What I’ve learned in 20+ years of building startups

What I’ve learned in 20+ years of building startups – Summary: The journey of building startups for over 20 years has yielded several crucial lessons:

  1. Fail Well: Failure is a common part of the startup process, with success in only a fraction of attempts. It’s important to accept failure as a stepping stone.
  2. Persistence: The key to overall success often lies in sheer perseverance and the refusal to quit, even in the face of early failures.
  3. The Power of ‘No’: Turning down opportunities, especially during financially tough times, is crucial to avoid burnout and stay true to your goals.
  4. Work Smart and Hard: While enjoying your work is vital, readiness to put in extra effort when needed is equally important.
  5. Start Slowly: For new businesses, especially online, it’s advisable to start small and avoid getting entangled in bureaucracy before proving the business model.
  6. Be Cautious with Growth: Rapid expansion can lead to financial strain. It’s better to grow at a sustainable pace.
  7. Avoid Corporate Pitfalls: As businesses grow, maintaining a customer-centric and enjoyable work culture is essential, avoiding the trap of becoming overly corporate.
  8. Embrace Remote Work: If possible, allowing remote work can save costs and increase employee productivity.
  9. Simplicity in Tools: Using too many apps and tools can be counterproductive. Stick to a few that work best for your team.
  10. Maintain Relationships: Keeping doors open with past collaborators is crucial, as business landscapes and relationships are ever-changing.

What I’ve learned in 20+ years of building startups – Lessons Learned in Detail

  1. Fail Well. You’ve heard it a million times before: ideas are easy; execution is hard. Execution is incredibly hard. And even if something works well for a while, it might not work sustainably forever. I fail a lot. I’d say my ideas are successful maybe 2/10 times, and that’s probably going easy on myself.

  2. Keep Going. The difference between overall success and failure, is usually as simple as not quitting. Most people don’t have the stomach for point #1 and give up way too quickly.

  3. Saying No. Especially if you didn’t have a particularly good month and it’s coming up on the 1st (bill time), it’s hard to say “No” to new income, but if you know it’s something you’ll hate doing, it could be better in the long-run to not take it or else face getting burnt out.

  4. Work Smart (and sometimes hard). I would hazard to guess that most of us do this because we hate the limitations and grind of the traditional 9-5? Most of us are more likely to be accused of being workaholics rather than being allergic to hard work, but it certainly helps if you enjoy what you do. That said, it can’t be cushy all the time. Sometimes you gotta put in a little elbow grease.

  5. Start Slow. I’ve helped many clients start their own businesses and I always try to urge them to pace themselves. They want instant results and they put the cart before the horse. Especially for online businesses, you don’t need a business license, LLC, trademark, lawyer, and an accountant before you’ve even made your first dollar! Prove that the thing actually works and is making enough money before worrying about all the red tape.

  6. Slow Down Again (when things start to go well). Most company owners get overly excited when things start to go well, start hiring more people, doing whatever they can to pour fuel on the fire, but usually end up suffocating the fire instead. Wait, just wait. Things might plateau or take a dip and suddenly you’re hemorrhaging money.

  7. Fancy Titles. At a certain stage of growth, egos shift, money changes people. What was once a customer-centric company that was fun to work at becomes more corporate by the day. Just because “that’s the way they’ve always done it” in terms of the structure of dino corps of old, that’s never a good reason to keep doing it that way.

  8. Stay Home. If your employee’s work can be done remotely, why are you wasting all that money on office space just to stress your workers out with commute and being somewhere they resent being, which studies have shown only make them less productive anyway?

  9. Keep it Simple. Don’t follow trends and sign you or your team up for every new tool or app that comes along just because they’re popular. Basecamp, Slack, Signal, HubSpot, Hootsuite, Google Workspace, Zoom (I despise Zoom), etc. More apps doesn’t mean more organization. Pick one or two options and use them to their full potential.

  10. Keep Doors Open. While you’ll inevitably become too busy to say “Yes” to everything, try to keep doors open for everyone you’ve already established a beneficial working relationship with. Nothing lasts forever, and that might be the lesson I learned the harshest way of all. More on that below…


What I’ve learned in 20+ years of building startups: A personal note that might be helpful to anyone who’s struggling

Some years back (around 2015), we sold the company my partner and I built that was paying our salaries. During those years, I closed a lot of doors, especially with clients because I was cushy with my salary, and didn’t want to spend time on other relationships and hustles I previously built up over the years.

I had a really rough few years after we sold and the money ran out where I almost threw in the towel and went back to a traditional 9-5 job. I could barely scrape rent together and went without groceries for longer than I’m comfortable admitting.

There’s no shame in doing what you’ve gotta do to keep food on the table, but the thought of “going back” was deeply depressing for me. Luckily, I managed to struggle my way through, building up clients again.

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What I’ve learned in 20+ years of building startups – Conclusion:

Navigating the world of startups requires a balance of resilience, strategic decision-making, and adaptability. The lessons learned over two decades in the startup ecosystem are not just strategies but guiding principles for sustainable success and growth in the dynamic world of entrepreneurship.


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What I’ve learned in 20+ years of building startups – References:

  1. Entrepreneurship Blogs and Websites: Look for blogs from successful entrepreneurs or business coaches. Sites like Entrepreneur (entrepreneur.com), Forbes Entrepreneurs Section (https://forbes.com/entrepreneurs), and Harvard Business Review (hbr.org) often have valuable articles on startup strategies and entrepreneurial journeys.
  2. Startup Case Studies: Websites like Inc. Magazine (inc.com) and Fast Company (fastcompany.com) frequently publish case studies and stories about startups and entrepreneurial experiences.
  3. Business and Tech News Websites: Platforms like TechCrunch (techcrunch.com), Business Insider (businessinsider.com), and The Wall Street Journal’s Business section (https://wsj.com/news/business) are good for staying updated on the latest in startup trends and business strategies.
  4. Remote Work and Productivity Tools Blogs: For insights on remote work and productivity tools, check out blogs from companies like Basecamp (basecamp.com), Slack (https://slack.com/blog), and Zoom (blog.zoom.us).
  5. Online Business Forums and Communities: Websites like Reddit’s Entrepreneur subreddit (https://reddit.com/r/Entrepreneur) or startup-focused forums on sites like Quora (quora.com) can provide real-world advice and experiences from various business owners.
  6. LinkedIn Articles and Thought Leaders: Following successful entrepreneurs and business thought leaders on LinkedIn can provide you with a plethora of insights and firsthand accounts of business experiences.
  7. Business and Entrepreneurship Books: Websites of authors who have written extensively on startups and entrepreneurship, such as Guy Kawasaki or Seth Godin, often have blogs and articles that are invaluable to entrepreneurs.

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What are the pros and cons of working as a software engineer for Google or Microsoft versus starting your own startup like Zoom or Uber or Airbnb did when they started out?

Google or Microsoft vs startup

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What are the pros and cons of working as a software engineer for Google or Microsoft versus starting your own startup like Zoom or Uber or Airbnb did when they started out?

Google and Microsoft are both giant tech companies that offer great benefits and salaries to their employees. However, they also have strict work schedules and can be inflexible when it comes to new ideas. In contrast, startups are often much more flexible and allow employees to have a greater sense of ownership over their work. They also typically offer lower salaries and fewer benefits, but the trade-off is that you have the opportunity to be more creative and innovative. If you’re the type of person who likes to take risks and be rewarded for your creativity, then starting your own startup may be a better option for you than working for a large corporation.

What are the pros and cons of working as a software engineer for Google or Microsoft versus starting your own startup like Zoom or Uber or Airbnb did when they started out?
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Google, Microsoft, and Apple are all giant tech companies that started out as small startups. Google and Microsoft both began in the garage of their founders, while Apple was started in a basement. All three companies are now worth billions of dollars. But which is the better option for a software engineer: working for one of these huge companies, or starting your own startup?

There are pros and cons to both choices. Working for a big company like Google or Microsoft comes with a lot of perks. These companies can offer competitive salaries, great benefits, and the chance to work on cutting-edge projects. However, they can also be inflexible and bureaucratic. Startups, on the other hand, are much more nimble and offer the opportunity to be more creative. But they also come with more risks, as most startups fail within the first few years.

Google/Microsoft

Pros:

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  • Top-of-the-market salaries.
  • Equity that is definitely going to be worth something once it vests.
  • Insane perks.
  • No risk. You have a very comfortable job that you can stay in for as long as you want.
  • You get all the tools and help you need.
  • You’re in a large community of like-minded engineers.
  • Having a well-known brand on your CV opens up many career opportunities.

Cons:

  • The work can be a bit mundane.
  • There is bureaucracy and petty office politics.
  • You have to answer to managers.
  • You won’t have a huge impact on the company.
  • It won’t make you rich. Just upper middle class.
  • Large tech companies often have questionable ethics.

Startup

Pros:

  • You don’t have to answer to anyone (except your customers).
  • It’s a very informal atmosphere.
  • It’s exciting. You never know what’s going to happen to the company in the next few months.
  • You have a huge impact on the success of the company.
  • You pick up many new skills quickly.
  • Building something from scratch is very rewarding.
  • If the company succeeds, you will become filthy rich.

Cons:


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  • Lower salary.
  • The company will most likely fail and your equity will be worthless.
  • You’ll experience constant setbacks until you reach product-market fit.
  • Your office perks are most likely limited to a coffee machine.
  • You have to do everything yourself, including tasks that you hate.
  • You’ll probably work longer hours.

To conclude:

Ultimately, it depends on what you want out of your career. If you want stability and the chance to work on some of the most innovative projects in the world, then working for a big tech company is the way to go. But if you’re willing to take on more risk in exchange for the chance to create something truly new and revolutionary, then starting your own startup may be the right path for you.

Some people tried everything from tiny startups to mid-sized companies to large behemoths. Based on experience, They’ve found that They very much enjoy working in startups, creating something new. But They’ve also been lucky to meet founders that value their skillset. It is always good to want to start your own company at some point, but the timing and idea has to be right.

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