8 Lessons From Second-Time Founders That Will Help Build Your First Startup

Derick David

Photo by Lala Azizi on Unsplash

A couple of weeks ago, I was in my own dedicated workspace at WeWork in Manila planning the next goals for my education startup.

As I do the planning, a question crossed my mind.

If a second-time founder were in my shoes, what would he or she be doing instead?

We can all acknowledge that second-time founders do 60% better than first-time founders. So, it’d be a hack to borrow a piece of their wisdom.

For instance, a major issue is that most first-time founders believe they need a perfect product to launch.

What you need actually is to build an MVP — a minimum viable product. This will allow you to test and validate your idea.

So, I went to one of the biggest communities for startup founders, entrepreneurs, and working professionals in the Philippines and I asked them a question.

The question:

The question gathered 52 responses in total, so I read and curated the best answers and made a summary.

If you’re a first-time founder, listen. Here are the 8 best advice by second-time founders on how to start your first startup.

1. Know when to quit on an idea or direction

When asked what is the best indicator to quit an idea, Mizael Pena, a second-time founder said that,

If it carries on too long without clear direction, it takes too many resources, time, and or energy, and no clear sight of when you may accomplish it.

This is probably one of the hardest to fathom since most founders fall in love with their idea and when they actually do, it’s hard for them to let go of it.

However, business is business. We have to learn that the idea we fell in love with isn’t working with, we have to consider putting it aside and move on, maybe with another one we’ll fall in love with.

It takes guts and a considerable amount of thought and research to make this decision, but when it’s done, it will be liberating.

Know when to quit on an idea or direction.

2. Spend less time on social media and more time with customers

Don’t do absolutely do this, unless most of your customers are on social media channels like Facebook, Instagram, and Twitter.

If that’s the case, then spend as much as time you want. However, even that you should be spending more time improving your product and iterating on actionable insights and feedback you’ve gotten from your customers or users.

If you have 2 or 3 people in your co-founder team, it’s best to assign only one of the co-founders to do the social media job.

The lesson here is to spend more time iterating on your product than you do marketing on social media.

3. Focus on work, clients, and strategic partners rather than wasting time on useless parlor tricks.

According to Bike Scouts founder, Myles Delfin,

What I learned doing my first two companies that I should have done from the start of what I’m doing now. I should have just gone with what I did before and focused on work, clients, and strategic partners rather than wasting time on useless parlor tricks.

When asked some examples of parlor tricks, Myles added,

Too many to mention, but for me it’s anything that takes the founder’s attention away from the fundamentals of his business: business development, branding, sales, client servicing.
Growth is often used as a compelling enticement to do “parlor tricks” that are often peddled by “experts” whose sole achievement is finding money to burn.

Myles is the founder of one of the biggest bikers communities in the Philippines and he said that it’s sad to see startups fail not because they had a bad idea but just because they tried to ride the short-term train when they really had to walk the long term road.

4. Get the right expert advice, either for free or with pay.

Marlon Valderama of LexMeet, a platform for finding the legal help you need, says highlight four main points.

  1. Read (theory/experience of others)
  2. Apply (act on the knowledge)
  3. Test (listen and emphasize)
  4. Iterate & Repeat

Step one, reading, is exactly what we’re trying to achieve with this article.

Step two is about applying what you learned from the experience of others.

Step three, testing your new assumptions and seeing if it works.

Step four is to keep iterating until you find the sweet spot of your product.

5. You don’t need to code to validate your idea

As a coder with more than 5 years of experience, I have to admit that there are days where you just want to start writing lines of code to test your idea.

As now an entrepreneur and startup founder, I realized that what you need to test your idea could be a simple sketch or an excel file.

Adriano Farano, Co-founder of Watchup and Stanford fellow, said that,

What you need is users! You can get users with a simple excel file or a spreadsheet.

Carlo P. Valencia, Founder of Startup PH training said that,

I wish I knew that I didn’t need to code the tech to validate the idea.

So simple, yet so true.

There are a lot of other ways to validate your idea, for instance:

  1. Blogposts
  2. Surveys
  3. User interviews
  4. Product Hunt launch

Additionally, all of these save you time and money.

6. Overcommunicate with your people and investors

According to Plentina co-founder, Earl Valencia,

The biggest lesson is to make sure you over-communicate with people and investors. It’s important to show them when times are tough as much as when times are good.

This advice by Earl also embodies the idea of building in public, where you show your work to your audience on social media starting from day one. Regardless, of whether you get failures and achievements.

The point we’re making here is that you have to apply and show yourself because people would want to see you doing the work.

Additionally, it helps you build relationships with potential partners, investors, employees, and customers.

As early you can do this, the better.

7. Work on the Partnership and distribution strategy that would strongly fit your model

How do you scale your startup? You don’t need to have a complete answer to this question, since your number one priority is to getting users and customers and improving your product based on their feedback.

However, it’s crucial to have an idea about your answer to that question. Especially, if you’re the CEO.

Angelo De Guzman, the founder of Cloudswyft, which is one of the biggest EdTech companies in Southeast Asia, not only in the Philippines, said that,

Work on the Partnership and distribution strategy (usually for scaling enterprise software) that would strongly fit your model.
Don’t be afraid to explore and test as many models as you can and learn from your mistakes that.
Get better every day, every week, every month, every quarter, and every year.

This is perhaps one of the most needed pieces of wisdom most first-time founders need because they typically work more on product development and design.

If you care about your company in the long-term just like what Myles Delfin emphasized, you have to keep iterating until you find the business model that is sustainable for your startup.

8. Find investors that add strategic value

For our final point, Angelo of Cloudswyft also adds that,

Focus on investors that would add strategic value to the business (if you are in raising capital mode)

It’s easy to find investors, but something hard to find the right investors that can add value to your startup other than funding.

This could be advisory, guidance, marketing, and network. When you manage to find an investor that knows a lot about your industry, like EdTech, it’s a massive hack. This will give you and your startup a headstart.

Angelo also mentions,

Hire wisely. Spend wisely. Be lean as much as you can. Invest in customer success. Be obsessive about end-user / customer platform support and acing lead times. under-promise and overdeliver

One more thing…

A month back, I was browsing around Paymongo’s website, a Philippine Fintech startup that is backed by Y Combinator and Peter Thiel.

I went over their social media channels and came across the co-founder, Francis Plaza’s post on the lessons he learned back in college.

Francis went to MIT and one of the lessons he shared gave me goosebumps. He said,

“Failing many times would eventually lead you to the thing you’ll do right”

Entrepreneurship, in reality, isn’t where founders are popping champagne bottles left and right and going to fancy dinners as a mark of their achievements.

When these happen, it certainly means that the founders are celebrating something, be that fundraising, revenue goal, new hires, or acquired users/customers milestone.

However, most fail before they achieve these. I’m afraid of failure, as most first-time entrepreneurs are. However, Francis’s advice made me fall in love with the idea of failing.

One of the reasons why the majority of people aren’t cut out for entrepreneurship is because they easily get discouraged when presented with failures or challenges.

And being bulletproof to it and having the ability to move forward to the next one is power. Now, I want to encourage everyone to fail, so that they appreciate success.


So what are the 8 lessons we can learn from these second-time founders that can help you build your first successful business?

  1. Know when to quit on an idea or direction

2. Spend less time on social media and more time with customers

3. Focus on work, clients, and strategic partners rather than wasting time on useless parlor tricks

4. Get the right expert advice, either for free or with pay.

5. You don’t need to code your idea to validate it

6. Overcommunicate with your people and investors

7. Work on the Partnership and distribution strategy that would strongly fit your model

8. Find investors that add strategic value

With all of these pieces of advice, it’s important to take note that at the end of the day, it’s your company and the final decision will come from you. Take it with a grain of salt of course. Results might vary depending on the idea, solution, product, team, and timing.

Comments / 0

Published by

10x Top Writer on Entrepreneurship, Innovation, and Startups.

New York, NY

More from Derick David

Comments / 0