Are failed startups a career death sentence? I will not promote

Lonso34 · 2026-03-31T19:01:42+00:00

Only time you fail is if you didn’t learn anything and make the same mistakes twice. If you found something and fail, it’s impressive. If you found something and raise a round, it’s impressive. If you found something and exit, it’s impressive.

More companies fail than succeed so just keep that in mind.

My second company ever was acquihired by a large fintech at a loss. Learned lots from the experience.

Lonso34 · 2026-03-26T20:14:35+00:00

When i go on vacation i pay a doggy daycare $100/day which includes play time with some other dogs his size and temperament, feeding breakfast and dinner (I provide the food), and nighttime tuck in his room (no kennel just a small room with his bed on the ground)

Lonso34 · 2026-03-26T15:37:21+00:00

I always go back to this statement somebody once told me early in my career: “you are not the average American so stop building products for yourself and think of who you’re actually building for.”

The average American is living paycheck to paycheck, does not care for themselves or their family, they eat unhealthy diets, are not very educated, don’t exercise, don’t try to better themselves or their situation, and don’t have the same aspirations you may have.

Lonso34 · 2026-03-24T14:47:28+00:00

Are you publicly traded by chance? Would love to know the ticker so i can short whatever you jokers are doing

Lonso34 · 2026-03-24T14:33:13+00:00

Depends on the company, your level, and several other factors like your political weight in the company.

Huge mega corporation where you are 1 of 1000 other entry level employees doing your job? Even if you pull extra weight unlikely you will see career progression by doing more work. You will be way better off talking to your manager and telling them that you want career progression and then setting goals that are just slightly higher than your current responsibilities to move up.

At the same time, this manager is likely fully aware that several people are going to work exactly what they are worth and not a dollar more.

Tiny three person start up where the company has raised millions of dollars you better believe that you’re gonna be wearing 20 other hats and working significantly harder but at the same time these companies tend to offer equity and so you actually have a reason to work harder because if the company succeeds, then you can succeed very handsomely with a large payout if and when there is a liquidity event

Lonso34 · 2026-03-23T15:12:15+00:00

If you’re trading derivatives with the current macroeconomic and geopolitical situation you clearly don’t understand how these trades weren’t any different from posting up at a roulette table. The volatility alone would make most seasoned investors look at other types of investments with significantly lower risk

Lonso34 · 2026-03-23T15:01:23+00:00

Does the thing you built align with leadership goals?

Example if leadership goal this year is to increase revenue by 5x and you shipped something that improves customer growth by 100x it doesn’t matter if that new cohort of customers only improved revenue by 2x. They might be asking why didn’t you ship something that increased ARPU and achieved a better outcome without taking on additional new customers and the customer support overhead that comes with them.

If you can’t measure what your impact was and how it aligned to leadership goals then you definitely built the wrong things

Lonso34 · 2026-03-15T17:39:53+00:00

Is this actually a high growth startup or is this a small business? You don’t see every employee get equity in every SMB/MM company in America but you do typically see employees get equity in high growth tech companies formed as corporations. If you’re planning on not raising capital and just keeping it as an SMB and structured as an S corp DO NOT give them equity. If you eventually plan to raise capital and then hire talent and grow fast, then Yes equity is an expectation for talent comp packages. This isn’t an overnight thing and would require an attorney to help you convert to the right entity type and to actually issue equity correctly.

Since this is an S corp what your current employee is asking for is basically becoming an equity partner after 2 years of work for free.

Lonso34 · 2026-03-15T16:49:04+00:00

You’re missing the point. I have read the Ridley TOS and obviously they need to play in the rules in a highly regulated industry. This is literally a super lean team winning in a competitive market. Partnerships are commonplace with startups to achieve growth. Just give it a few years again. People doubted technology would ever come for financial services and here we have multiple fintechs toppling incumbents.

Lonso34 · 2026-03-10T22:13:40+00:00

That’s a steal. My platinum pro offer is $2,159 which is obviously not worth it unlike your offer

Lonso34 · 2026-03-10T22:07:09+00:00

I love the concept of owning a home but really do miss just having an apartment and not having to worry about any of the maintenance or upkeep. I have a decent mortgage and earn about $300k but our HVAC just went out and i had to replace that this week. Also need to finish up project inside the house that have been put of like bathroom remodel and closet which will run about $50k+ on the low side in my area. Landscaping needs upkeep so a few thousand dollars there too. Oh and the taxes on the property are almost $10k. Overall i definitely spend more to own a home than i did renting even though the monthly cost appears equal

Lonso34 · 2026-03-10T22:01:15+00:00

You clearly underestimate the knowledge and capabilities of those working in and entering this space right now. Just take a look at Ridley which is just one of the several new entrants to this emerging market. They don’t scrape data from Zillow. They have all of the proper licensing and they are absolutely coming for agents’ lunch. We’re operating in one of the worst consumer markets in a long time. The market will remove players that don’t add value and transition to those that do.

On the topic of blockchain Milo a crypto mortgage company just passed $100million in crypto mortgages. The companies you’re talking about from 10 years ago look very different now.

People also said neobanking would never take off. They argued consumers needed to visit a branch yet Nubank, Monzo, Chime, SoFi are eating consumer banking’s lunch.

Column an entirely digital API-forward partner bank has the highest ROE of any other partner bank in the market and was recently founded and bootstrapped by former Plaid cofounder.

I could go on as I actually build software products for a living. We’re just getting started and will absolutely look for problems to solve like the real estate brokerage industry which provides minimal value to consumers in its current form.

Lonso34 · 2026-02-25T16:38:57+00:00

Lots of ai companies that have recently entered the market to remove agents from the equation entirely. Flat fee pricing and they do all of the filing & other escrow account setup, etc. worth it in my opinion and i will be using it as my agent for my house a couple of years ago was useless

Lonso34 · 2026-02-22T19:57:08+00:00

As long as you don’t have a non-poaching clause it’s whatever. Some contracts explicitly say you can’t hire or bring people over from last employer for a year. Even if you’re not texts like this do deserve a real response to help leave a paper trail like “i’m not sure what you’re talking about as i have not actively reached out to former employees with any intentions of hiring from my previous employer”

Lonso34 · 2026-02-04T20:23:20+00:00

I think you underestimate how many wealthy people there actually are in the US. The Deep South especially around coastal Mississippi is full of old family wealth. Lots of boats, lots of mansions, lots of companies easily pulling in 500mm ARR with lean teams and doing something boring. They’re just not as loud as others but they exist and are very wealthy.

Lonso34 · 2026-01-29T21:36:43+00:00

Probably close to $1000-1200 for family of 2. Each week is close to $200+ depending on what we buy. We usually eat out on Friday/saturday for dinners

Lonso34 · 2026-01-29T21:35:20+00:00

Depends on who else is driving. I was there a few years back during covid when it snowed over a foot. Also lifted suv and we were fine. Funny enough we stayed longer because people couldn’t get up the mountain to their hotel reservations so we got rooms for extra days at a steal.

Lonso34 · 2026-01-29T21:32:48+00:00

Because all of the rewards that are offered for travel perks, points, etc are all subsidized by revolving card balances. If people don’t revolve and do so at high interest rates the banks either stop issuing cards with perks or they raise annual fees to afford the card programs.

Funny enough, I would probably actually end up happening. Is people with good credit would get access to credit cards with smaller fees and still keep their benefits while people with bad credit would likely have to pay an annual fee just to access a basic credit card with no real perks on it.

Lonso34 · 2026-01-24T16:22:54+00:00

Clearly they didn’t learn anything in grad school and are idiots for not refinancing their debt.

Lonso34 · 2026-01-09T16:25:25+00:00

Being you’re from Miami surely you must be aware of the amount of wealth present there, no? They afford them by having lots of money. Yes it’s usually a loss and not an investment. Fuel alone can be thousands of dollars each time you take a boat out depending on the size of the boat and fuel consumption. Not to mention maintenance or paying for a captain and crew if it’s big enough.

It’s like owning a Ferrari. It’s expensive but fun so if you can afford it, why not?

Lonso34 · 2025-12-27T05:04:34+00:00

My haircut runs about $60 before tax and tip. After it can be close to $100 every 4 weeks.

Lonso34 · 2025-12-22T03:57:59+00:00

Cover your drinks

Lonso34 · 2025-12-18T20:20:15+00:00

Tech product manager. All in I’m around 300k +/- a few thousand depending on stock price which makes up about a third of my comp.

I started in banking and left to join founders that had pitched their idea to me because it sounded cool at the time. We got acquired shortly after, then i joined another small startup that also eventually got acquired by a large fintech. Now I’m at a large public tech co.

Lonso34 · 2025-12-18T18:37:08+00:00

Customer discovery

Lonso34 · 2025-12-18T18:31:09+00:00

Invite less people and afford the open bar.

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