Top 10 Lessons for 2nd/3rd Time Founders: Actionable Insights

Discover actionable insights from a seasoned 2nd/3rd time founder. Learn the top 10 lessons on product development, marketing, pricing, and team management. Avoid common pitfalls and drive your SaaS startup to success with these practical tips.

Top 10 Lessons for 2nd/3rd Time Founders: Actionable Insights
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Jul 15, 2024 11:44 AM
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Nov 6, 2023
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What are your best lessons learnt, as a 2nd/3rd time founder?

I did a Reddit AMA on r/SaaS last week and this question really made me stop and think deeply.
I've tried to make sure this advice is actionable and isn't generic.

My #10 lessons (non-exhaustive)...

#1 Getting the basics right from day 1:

  • Product/architecture (not too simple, not too complex)
  • Implementing usage analytics and A/B testing from day 1
  • Slick on-boarding, follows best-practise
  • New user email campaigns (personalised on sign up stage)

#2 Defining up front how to know if a new feature is having the right impact after release.

Ask yourself, "X weeks after this feature launch, how will I know, objectively, whether it's had a +VE impact on the product?".
Released so many features & been clueless afterwards.

#3 Not over-perfecting new features, launch them basic and then launch v2, v3, etc. versions of a feature.

So easy to over-polish a feature for weeks to then release it and it flops or people use it in ways you never imagined.

#4 Not over-investing in paid marketing too early on.

Just because you have the money to spend on this, doesn't mean you should. I've given @facebook too much money on product that didn't have PMF.

#5 Change pricing plans to test impact on conversion.

So many startups set and forget their prices.
I've always been too scared to do pricing tests before. Changing your pricing is scary. But no other way to know if you're over or under-charging.

#6 Only have meetings when essential. Always have an agenda.

  • Meetings always fill their alloted time, so shorten them
  • Agendas might feel formal, but it gives a clear plan for the meeting and stops digressions
  • Share agendas before the meeting

#7 Moving on quickly after disagreeing with a co-founder. And know who should make the final decision on any matter.

It's business, not personal. So don't make it personal with your ego.
Have clear ownership areas, e.g. "Kate will make the final decisions on product"

#8 Minimum Loveable Product > MVP.

The term "MVP" is 20+ years old. Tech and the web was very different then.
Standards are significantly higher now across the board. If your product doesn't look nice, it makes it feel cheap and unreliable.
How? Do less, but do it well.

#9 Your current customer base is a very small % of your total lifetime # of customers.

With that fact, don't delay or avoid big decisions because it might disrupt your existing customer base. Do what's right for the medium+ term, even if it generates a bit of short-term noise.

#10 Less is more.

This proverb is almost always right, whether you're thinking about:
  • Landing page copy
  • Product features
  • Feature functionality
  • Metrics to track
  • Slack messages
  • Explanations of anything to anyone
Put in the work to be concise — save everyone time.

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Written by

Alex Rainey
Alex Rainey

Alex is an experienced CTO and founder who largely focuses on all the technical areas of My AskAI, from AI Engineering, Technical Product Management and overall Platform Development.