The realities of bootstrapping a startup

Crissi Cole
4 min readApr 27, 2021


Every other person I talk to about my new startup wants to know one thing: What is it REALLY like? Is it nirvana? Ya, no.

It’s absolutely amazing, freeing, and terrifying, all at the same time.

At Penny, we share the wisdom. We get the finance&investing trade secrets out in the open, so women can play the game too. Why shouldn’t I also do that with my personal journey in startup-land? Here you go — raw and real.

Timeline [I am 8 months in, and just launched a v1 beta product]

July 2020: Quit my job

August 2020: Took the month off to recharge (you should take longer, btw)

September 2020: Business plan / brain dump of financial know-how

October 2020: Started coding a prototype / user interviews along the way

Nov & Dec 2020: Worked on branding / copy / marketing while working with dev team on product

January 2021: Made key hires / realized my product is 10x harder to build than we thought…aka delayed.

February 2021: Brought on new tech talent / launched social media

March 2021: Test test test, fix fix fix

April 2021: Launched v1 beta product to 300 women 😬

[entire 8 months: watched my bank account dwindle — as if there wasn’t enough pressure and stress already]

Realities & Advice

1.Comparison culture is brutal — you will find yourself looking at Series C,D,E startups and get frustrated that your product doesn’t look like theirs yet. Of course it doesn’t. They’ve been building for 5–10 years. You can’t build it all in a day. Compare yourself to yourself, not to others. You don’t know what you product needs to be, your customer does. Challenge your thinking and assumptions, not your progress against someone who has been doing it way longer. Stay laser-focused on your problem, and your customer, and that will drown out the judgements.

Excerpt from my founder journal (Yes, you are going to want to journal or your friends&family are going to get sick of your startup real quick)

2. You’ll have to make hard decisions all damn day. You’ll feel uncomfortable and unprepared more than not. You’ll have to ask for help more than you want to. Get yourself some amazing strategic advisors early on (use a FAST), join a startup community (I did OnDeck), and if you find yourself thinking about a particular problem for more than a couple weeks — it’s probably a gap in your biz, so make it a priority to find a solution and move to the next thing.

3. Your brain never shuts off. Once you’ve lit the fire on something you love so freakin’ much, it just burns brighter. That is awesome, because you need it to fuel you, but it makes resting almost impossible. Your mental clarity is the most important piece of the puzzle, and you can’t let anything or anyone take that away from you. We all need rest. More work doesn’t = more productivity. Figure out how to recharge.

Thankfully I have a husband that reminds me when it’s time to lock the computer in the drawer.

4. You will feel disorganized, and behind, all the time. If you know me at all, you know I have a list for everything, have a zero inbox , and (used to) prepare for every meeting. Forget all those things, and get used to constant chaos. The only list that matters is the list of 3 big things you are shooting for in that week. I always have that on a sticky note on my laptop.

5. Things move so fast and so slow all at the same time — some things you have to hold back because you don’t want them flying out the door without an extra double-check, while others seem to take forever to solve. That’s the name of the game. Just go with it. Messy is good. Sequence is what really matters. You can’t put a door on a house that has no framing. Figure out what the foundation looks like, pause, figure out how you are going to pour the foundation, and go. Don’t cut corners on the things that make your product special. That’s the whole point. Heads down and then when you are close, lift your head up and figure out the next thing that needs to happen. Do this 100x over and you are a founder.

6. The rollercoaster is worth it — if you don’t feel challenged or intellectually stimulated in your job, or are bored out of your mind, or if you look out in the world and wish you could fix something, or have this wild curiosity to create a different life for yourself and others, then do it. And if you are using your own money to get the company off the ground, you’ll spend wisely, and feel seriously accomplished when you have a working product out in the world.

P.S. My company is Penny Finance, an early stage startup that is taking on the wealth gap. We want every woman who doesn’t have a financial mentor to have Penny. She is my first born, and I love her so much words cannot describe. You can follow us here.



Crissi Cole

Founder and CEO, Penny Finance. Former VP @ Goldman Sachs.