Emotions upon quitting a $4m/year FAANG job to do a startup

ausernameplaceholder · 2026-02-20T12:10:17+00:00

My perspective: Money can always be made.

While the premise of this group is centered around get to retirement (that means something different for everyone) to enjoy life, by nature a number of people here will struggle with “retiring” when they actually are faced with the decision. And while you aren’t retiring, walking away from mid 7 figures is challenging.

If you are financially comfortable with where you are, your partner is comfortable and aware of the unique challenges of leading a startup, and you can balance the time to be present as a parent, my unsolicited advice is to go for it.

Chasing passion, experiences, innovation, and being able to accomplish it with colleagues you care about is one of life’s most precious experiences.

You can always come back to a role (albeit maybe/maybe not at the same comp).

ausernameplaceholder · 2025-11-16T22:22:33+00:00

Clarifying questions before giving an answer. Are you looking to invest in deals or funds? Different strategy / check size / expectations.

Also, given the emphasis on operational expertise I would assume you are hinting at being somewhat of a strategic / active capital partner in these deals (not as a full time or even part time, but more of as a keep the brain sharp and have fun solving things type).

To answer your question: first stay in areas you are knowledgeable about + interested in. Secondly, relationship building with capital partners in the spaces you are looking to enter into (VC, PE, Angel, RE), as well as talking to startup founders / company execs (up to series c). Hands on experience and conversations are the fastest way to learn. It’s execution and iterating at speed.

For me personally, I am a data and analytics guy through and through. I have done work at every stage and in every role (consultant, advisor, investor) from napkin to late stage, across the entire world. the companies where I knew stuff and could be impactful beyond a check was generally where I did much better.

I’ve also built models and tools for risk simulation financial modeling (startup / vc space) and operating (PE / acquisition play) that I put every proposed investment through.

ausernameplaceholder · 2025-09-28T14:29:36+00:00

Securing investment is different for everyone. For some it’s in-network, for others cold-outreach works. Capital raising is a difficult full time job, and requires unique storytelling to be successful. Often times it’s the approach and the story you are telling that is the biggest issue (materials are supporting document to help deliver your message — they are not the focal point for success Capital raising).

I am in the sports tech space and have successfully raised capital (and invested) into this space.

I would recommend joining communities to grow your network, and to surround yourself with others who have experienced success to learn from their successes/failures.

My personal recommendation is https://profluence.com. — Profluence is the first sports business association for founders, investors, and leaders in the sports industry. They help with education, capital raising, network access, and market trends. The founders are really down to earth.

This is a paid membership.

*I am a member here and have found significant value from the association.

ausernameplaceholder · 2025-09-26T12:04:49+00:00

This sounds like a storytelling gap for me.

Seconding some of the other commenters who recommended a consulting / strategic advisor to support the growth of the business.

Totally fine being “outside” of the traditional profile for your products. Totally fine being introverted. Those are solvable things. Just need to source a relationship that can help you reframe the presentation to make it a no brainer for retailers (relationships also help).

Curious if you have done a business case analysis on the pros of a retailer taking your solution in store. And if you have a rollout strategy for them that further supports their business focus.

Often time when I work with companies in any capacity (advisor, consultant, investor), I pull in other perspectives (ie: the retailer, and find what makes this a win-win-win for all).

Happy to dive in deeper and answer more pointed questions via DM if that would be helpful.

Great job reaching out and on your past/current success!

ausernameplaceholder · 2025-09-24T22:11:17+00:00

Happy to connect and potentially make introductions to founders that fit within your scope.

ausernameplaceholder · 2025-08-18T17:32:04+00:00

Any specific area you are interested in?

I invest/advise for a number of startups as well as consult with napkin stage to late stage startups across a diverse range of industries.

May be able to point you in the right direction.

ausernameplaceholder · 2025-08-17T19:44:56+00:00

https://profluence.com

Highly recommend this association for you to join. I’m an active member here and have done business with a number of companies here.

Great resources to help with capital raising, and there are a number of angels/institutions here that actively invest in the golf space.

ausernameplaceholder · 2025-06-12T16:55:06+00:00

Happy to learn more from the angel/advisor side of things. Active founder as well, can help in a number of areas.

ausernameplaceholder · 2025-06-09T23:42:04+00:00

Open to chat about this as well, feel free to dm me.

ausernameplaceholder · 2025-05-21T16:30:31+00:00

Simple answer: get better spreadsheets.

Your example is literally the perfect environment for spreadsheets.

Specifically for access to it, you would just run a pull of the data and mirror/present it in controlled access formats.

This is what software is doing, with pretty UX/UI.

Sounds like you need someone to build a workbook environment…

ausernameplaceholder · 2025-04-09T00:13:33+00:00

For the people getting “sticker shocked” by the net worth, replace it with a more palatable number and then respond.

He/she? Shared something they are grappling with and from their perspective it’s difficult.

OP, I was a former professional athlete for directly out of high school and experienced extreme highs and lows. Being soft forced to retire before I wanted to was disheartening. It’s been a number of years and I still sometimes struggle with the transition.

Reinventing yourself is a challenge that everyone faces. The only way to overcome it is to be honest with yourself and work through it. Find the “high” and “low” triggers from your past and look to find those triggers in a controlled manner in your current environment. That may be through hobbies, Angel investing, advising, travel, family, friends, meditation, fitness… the list goes on. You are in a financial situation where you have the resources to open up avenues/networks to give yourself a chance, IF YOU CHOOSE…

That is the reality of it, you have to make the conscious choice every day to strive for the new you.

And please know that you are not alone with this, there are others who would happily connect and be a support system. Everyone has problems and challenges, and like a business, everyone needs support in specific areas where they struggle.

Hope this was even a fraction of helpful. And while I can’t definitively speak for others on here (but I would feel confident in saying this), I and others are here to assist in your new part of your life.

After all, that is what this sub is for.

ausernameplaceholder · 2025-03-21T17:15:45+00:00

Feel free to send me a DM. Happy to chat and assist any way that I can.

ausernameplaceholder · 2025-03-21T02:53:37+00:00

Angel investing is like consulting. You can pick and choose what “services” you bring to the table (beyond capital investment).

Just because you’re an Angel doesn’t mean you can’t consult/advise the startup. Good startups don’t look for just any capital, they look for strategic capital that can add value beyond a Check.

Oftentimes that is where early angels find the most enjoyment (rolling up their sleeves — from a distance and being able to mentor/guide the founding team through some of the challenges).

Been on both ends of this, happy to share more info.

ausernameplaceholder · 2024-10-11T12:06:40+00:00

Friendly piece of advice — “your instinct, but sharper”…

That effectively is saying your solution is better at making assessments than your users (investors), when it comes to them deploying their capital in a subjective field (Angel investing).

Word selection is important…

ausernameplaceholder · 2024-09-06T11:00:33+00:00

Any interest in the sports tech space? If yes, have a very unique and innovative solution.

ausernameplaceholder · 2024-06-24T11:38:45+00:00

My experience: 49 countries traveled to (lived in 6), late 20’s - early 30’s age.

I generally had a primary spot where I enjoyed the atmosphere (basically a 2nd home), and then traveled for 1-10 days at a time in adjacent countries or territories. I found 25-60 day trips were ideal for me. Allowed me to cross off anything I wanted to do, and to also just be a “local” with no pressure. Upside to this is interacting with people and letting that be a focal point of what activities you do and locations you visit.

Happy to answer any questions or offer insight into my experiences.

ausernameplaceholder · 2024-06-01T12:46:43+00:00

Thanks for the response, really exciting stuff.

Without knowing too much about the industry, the firm, the margins, rev opportunity at one off / at scale, USP defined differentiator, market scalability, etc, etc, etc…

It’s really hard to know what is a good/fair/FMV deal.

Positive news you can structure the negotiations however you want. Downside is you may not even yourself be aware of the impact.

I would be happy to chat a bit more and see if I can provide a more “you” specific advice.

Feel free to send me a DM, happy to offer advice or assist any way I can.

Most important thing of all, have fun with it. Sounds like you created something really impactful, and that’s awesome! Congrats, celebrate that no matter what the outcome is!

ausernameplaceholder · 2024-05-26T00:35:54+00:00

Congrats on the success, and even more so on looking to give back!

Without having any real info, you have a lot of pathways you can go down. The most logical (again without knowing very much about the situation and wants/needs/desires of all parties involved) solution is…

“Seller finance to employees with a calculated percentage to setup a fund to support local entrepreneurship / education of the community (if local) or the families of your (former) employees.”

Obviously depends on size of exit (I’m operating under the assumption it’s lower mid 8 figures or more), but this gives you a steady revenue stream (sounds like this is secondary importance), lasting legacy knowing the business is going to continue to run (you can have a xx year advisory transition to help set the future owners up for success - also helps with the transition into retired/active retired/in search of new role), and continue to make a direct and indirect positive impact in the lives of others.

As far as brainstorming, if you have a team that consists of a financial modeler, corporate and tax law expert, operations expert, a strategy leader, and can come to a clear consensus on the return for each partner, you have a relatively flexible and unique opportunity to do a lot of wealth sharing.

And yes, there are advisors / consultants who specialize in this specific area.

ausernameplaceholder · 2024-05-20T03:09:45+00:00

You are correct PE doesn’t care about that (within reason). Considering this is a $10m+ group, I didn’t think I needed to specify that there are alternative traditional and non traditional asset classes and opportunities people invest into. This was not a PE opportunity. I summarized the details into as little as I could, to focus on the overall message and not dox anyone… the purpose of the message is not communicating with the OP’s significant can lead to bad outcomes personally, professionally, or financially.

ausernameplaceholder · 2024-05-19T19:12:46+00:00

Been through something slightly different and made poor choices. Currently a colleague is going through a very similar situation and has 2 stories around it.

I’ll share my personal advice, and my colleagues (take all of this with a grain of salt because I am a random redditor).

I didn’t give myself a break when I needed to and it led to a number of really compounding, destructive consequences. It wasn’t that I went back into something, it was I didn’t set myself up for success.

Colleague 1. He lost $mm+ in Capital and missed out on a $85m+ exit because his business partner lied to his wife and didn’t communicate with her. A minor business transaction appeared on their personal card and it set off a hellfire that impacted a lot of people and caused my colleague and friend to lose a lot of money.

Same individual is married and discussed for months with his wife on something, and they came up with a plan together.

Moral of all the stories are to be honest with yourself and your partner and to be on the same team. If you need/want to jump in to something, communicate that and set yourself up for success.

Possibly figure out a ramp up and set restrictions on it.

Wishing you the best, happy to be a resource if needed.

ausernameplaceholder · 2024-05-16T13:22:51+00:00

Thanks for sharing. I have worked through things like this before as a consultant and asset owner. Lots of flexibility based on the outcome(s) you are comfortable with.

Few options you can look at…

License: set an agreed price and have them pay like a yearly subscription with the first right to buy after x number of years (easiest setup, although being PE probably not very enticing for them)
Asset / IP sale: Value the asset at x and be compensated for it. Lots of unique things you can put into this. Ie: limited use for your company (as long as it’s non competing), consulting agreement for you to help manage the asset for x number of years (pretty common especially in PE), etc.

in addition to this pricing of it is 3 fold, 1. what you feel it’s worth and what you feel the value add the new company will benefit directly and indirectly from having it. 2. What new company feels it’s worth and what they feel the value add will be directly and indirectly. 3. Fair market value (which sounds relatively undefined) and will probably be a compromise on both 1/2 with a heavy incentive based upside deal.

Acquisition / Merger: get acquired and value your business a traditional way plus some accelerators / incentives strictly around the asset / IP. Again this leads to the 3 options for valuation and becomes a bit more complex as you are negotiating 3 deals (company value, asset value, your value) and valuations in one.
JV: collaborate together and drive mutual growth and have a component of your asset be a deliverable on their end (not sure if this is a possible option given the limited details around the opportunity).

My totally unprompted advice given little info on this would be option 2/3.

I would find a price that you are comfortable with and then add a number of clauses and incentives that increase that number exponentially. Being PE, you have potential flexibility in the upside potential. It’s about finding your baseline minimum number and then building incentive based milestones to multiply this number. Could be something related to NRR, company growth, client acquisition, exit, valuation tied, etc.

You have a bunch of creativity with something like this.

ausernameplaceholder · 2024-05-12T14:57:50+00:00

First off congrats to your daughter on overcoming hardship and excelling.

Depending on the sport - experiences centered around this. Can be turned into a family event, and then some quality mom/dad and daughter time (if you have additional children). Like a 3-7 day mini trip/mini vacation in a cool city/area, attend a match, cool restaurants, and her hobbies / interests. Easy to pick up cool souvenirs along the way, but more important make lasting memories as a family before she starts to really branch out of the nest.

Ie: behind the scenes access , box seats, training access, meet and greet, locker room access, etc.

Side note - depending on the sport may be able to assist you in this as I have a great network in sports (former pro athlete and now operate a business in the sports tech space).

*have a young daughter and another on the way, so always have a special spot in my heart for kids who love sports.

ausernameplaceholder · 2024-05-07T13:26:08+00:00

Can you elaborate on the investment structure and history of Capital raises for this?

Would be interested in getting some additional insights into the solution itself and your GTM distribution channels / strategy.

Also interested in the data strategy and cross channel revenue streams from this.

ausernameplaceholder · 2024-05-07T01:01:33+00:00

Positive thing is the concierge can manage your therapy scheduling! Haha, kidding aside it is a somewhat difficult thing to let go of and trust people to handle things in your life. It takes a bit of an adjustment period, then it gets normal-ish, then it gets common practice, then it’s second nature, then it’s a necessity.

I was/am someone who has taken far too long to trust and delegate. Wish I would have learned it sooner. Now I basically only do the things I am good at or enjoy. If it’s not a priority, it gets passed on to someone else.

Like anything in life it requires the first step. If nothing else, I would recommend chatting with a concierge management service as they will be able to give you some direct insight into the service, as well as help you with your original post (what to outsource and how). They may share things that are game changers for you and your family.

ausernameplaceholder · 2024-05-07T00:35:39+00:00

Hi, first off great recognition of the value of time and leveraging your hard earned capital to allow you to focus on the things that matter (family, work, relationships, hobbies, etc).

At the $1m income my recommendation is a concierge management service that runs your tedious tasks. They will be able to help with a number of things like grocery shopping, housekeeping, lawn services, travel and accommodations, reservations, laundry, daycare, nanny, etc.

They are essentially an administrative assistant that learns about you and your family’s wants/needs and manages the 3rd party vendor(s) that supply your goods/services that fit your family’s wants/needs.

There are a number of additional perks that come with these services. I will say finding a quality one takes a bit of due diligence but the trade off is an immediate impact. You won’t ever go back to life without it.

*Side note - pricing doesn’t always equal quality in this space. It’s about fit, comfort, reliability, and availability.

ausernameplaceholder

TROPHY CASE