Job vs StartUp: 3 Mental Models to Decide

I was fortunate to have strong leaders from late-stage startups and established corporations join us early in WhiteHat Jr. They built the company to scale. Are you thinking of building your own startup/joining a very early stage startup?

Your decision can change the destiny of thousands!

And yours too.

Here are 3 mental models to help you decide whether you should startup or continue in your job, which I used in my own deliberations-hope they’re of some use to budding entrepreneurs:

3 questions to ask yourself

1. Where will you learn the most? The 20×4 Rule

I started WhiteHat Jr after a 17-year corporate career in traditional organizations like P&G, Discovery etc.

And going back, I probably wouldn’t change that.

All startup founders (including me!) would like you to believe that only startups give 10x growth. But late stage start-ups/corporate careers give a few, key 10x growth opportunities that startups can’t:

A. New Geographies

B. New Industries

C. Turning Your Hobbies into Mastery

Example, I learnt tremendously in my early career from moving from India to Philippines, US etc as well as shifting industries from consumer goods to consulting, then media.

But point C above was perhaps the most significant for me.

I couldn’t have written my novels or gone very deep into hiking and yoga if I’d replaced the steady rhythm of a corporate career with the manic intensity of a startup too early. And my life would be a mere shadow without these!

Are you growing 20×4 from shifting countries, industries, or gaining mastery in pursuits of the soul?

“Replace 20 years of low-intensity work with 4 years of high-intensity work–and compress 20 years of personal and professional growth in these 4 years.”

Then, a late-stage job can be as good as a startup!

If not, leave as soon as you can.

Because the external world eventually rewards your internal growth. Startups are vehicles of extraordinary, often involuntary, compressed growth. You can have the same outcomes by voluntarily choosing 20×4 growth in a corporation.

Just choose growth over stasis.

Systems are inefficient in short-term but incredibly efficient in long-term. And long-term they’ll always reward growth.

2. Do you have a burning need for financial freedom? The 4% Rule

I hadn’t cared much for money until my mid 30s when I realized that I wouldn’t be able to lead the wanderer’s life as I entered my 40’s. You couldn’t be a CEO or a senior leader, walk out for a couple of years to write and travel, and then come back again, expecting to be a leader again.

I had to be financially free to live my values of independence and growth.

How much do you need to be free?

Fortunately, there’s a mathematical versus spiritual answer to it!

You’re free if you can live off 4% of your Liquid Net Worth annually for the rest of your life (Bengen, 1994)¹.

Rationale: With reasonable investing, you can target getting a 4% return on your investments, net of inflation and taxes, annually over a long-term. So theoretically, you don’t need to touch your principal amount, which becomes a safety net, except to weather short-term ups and downs of investing cycles.

What are your projected all-in annual expenses for the rest of your life?

4% Rule= Assume they’re Rs 25 lakhs per year, then you need Rs 6.25 cr in Net Worth to be free.

You can calculate your freedom number here (no data collected for any use).

Is financial freedom your burning goal? Then, stake it all and startup/join a very early stage start-up. You’ll achieve Financial Freedom early only with equity ownership vs salaries, no matter how high the salaries go.

3. Can you afford the risk?” Salary/14 lakh” Rule

I’ve often seen oversaving to be a more common problem than overspending among most of my IIM and college classmates.

Trade savings for growth often.

Can you afford a major salary cut to start on your own*?

Use the Salary Divided by $20,000 Rule, (First Transitions Study: 2005) or (Your Salary in USD)/($20,000) is the number of months you need to find a job if your startup doesn’t work out.

You can calculate your risk tolerance mathematically. First, calculate how long your savings will last, based on your Total Liquid Savings and All-In monthly expenses. Then, subtract the number of months you’ll have to look for a job based on the (Salary/$20,000) rule.

Months to Pursue Your StartUp Uninhibitedly= (Liquid Savings/Monthly Expenses)-(Salary/$20,000).

In India, I changed it to the (Salary/Rs 14 lakh) rule², which guided me equally well for taking risks when I moved to India.

Later, when we had kids, I changed the rule to $10,000 or 7-lakh rule to give myself more cover and double the time to look for a job.

You can calculate your risk timeline by putting your exact numbers in this calculator here

Do you have enough months to take the startup risk based on the calculator above? Then, go all out for it!

*Please drop me a note in the comments if you want more data on how much to pay yourself in a startup. I’ll send details of investor approved founder/co-founder salaries in early stage start-ups.

Finally and most importantly, does the startup’s mission excite you to give it your all? The “10,10,6” Rule.

Our management team was in the office together for 50-60 hours when we were launching WhiteHat Jr in the US as we managed operations in India, then US, and back.

I didn’t think I would have the energy for these night-outs as a 40 year old. But I hadn’t experienced the daily start-up adrenalin flows from a team united on a mission before!

For much of the early years, all the core team worked on a rigorous 10x10x6 schedule, 10-to-10, 6 days a week³, without really feeling the strain.

Have you found a cause bigger than yourself?

One where you can’t breathe until you make it come to life?

Then, ignore all the models above and dive in fully! Your one decision can change the trajectory of thousands!

“Make mistakes of ambitions not mistakes of sloth.”- Machiavelli

Please let me know in the comments if the models are useful to make the decision–and also, if you want early-stage founder salary data. And if you found this useful, you will also like this new YT Video (<5 Minutes) on The One Exercise to Find Your Purpose in Life.

Please subscribe to the channel here for 3x new videos/week on startup and success models.

¹William Bengen, 1994. India 10-year Validation: (Sensex Return- Inflation-Taxes)~4%.
²Straight Dollar conversion from $20,000, triangulated with anecdotal evidence. Please drop a note in the comments if you have access to better research for India so I can update the blog!
³Inspiration: Jack Ma AliBaba’s “9,9,6”.

*Please drop me a note in the comments if you want more data on how much to pay yourself in a startup. I’ll send details of investor approved founder/co-founder salaries in early stage start-ups.*