[Somewhat] Comprehensive Guide to Avoiding a Doomed Startup

Inspired by @UrAssIsSaaS 's great thread ( https://bravado.co/war-room/posts/comprehensive-guide-for-moving-to-a-startup ) I wanted to provide an alternate perspective.


It's important to remember that 90% of startups fail.


I say this not to be overly negative, but as a reality check to those evaluating gigs at startups. Especially people earlier in their career. Startups LOVE to "prey" on naive employees by selling them a dream of equity and ringing the bell on Nasdaq. 99% won't make it...


Having worked at several failed startups (along with two that have exited -- one IPO and one acquisition) it's important to spot the red flags and know when to bail.


I'm about to leave a startup after 3 months because despite buckets of money from prestigious VCs they're bound to fail. 


Here's what to watch out for...


1) Burning through cash -- Swanky offices are great for impressing candidates and potential clients, but all that La Croix adds up if you're not bringing in revenue. One startup I worked at leased a HUGE office based on their growth plan, only to end up subletting space to several other companies and converting their office into a co-working space after 6 months. Frugality (especially with other people's money) is a virtue.


2) No proven product/market fit -- Do they have customers? Are their customers friends and family? VC connections? Have they proven there is demand for their product with potential clients? Lots of ideas sound great on paper, but if no one is willing to pay for them you're gonna have a bad time. I learned early on that if prospects reaction to your demo is "this is cool" then you're fucked. No one buys "cool" products. They buy products that address quantifiable business pain in a differentiated way.


3) Shaky business model -- What is their plan? Hustle 24/7 ain't a plan. Someone with real world experience should have a spreadsheet that models everything out and shows how they'll make money. Huge red flag is the business model isn't codified or if they seem to pivot every 6 weeks. Even bigger red flag if they're under-selling themselves and bringing on clients who are costing them more than they're worth.


4) Shitty founders -- For the most part, you want to find an executive team who has done this before. Inexperienced founders make a lot of mistakes, and if the product is their "baby" they're often shut off to feedback or criticism. If they think they're the smartest person in the room, that's a bad sign. The successful founders I've worked with are intellectual, humble, and tend to be quiet. The failed founders I've worked with find every opportunity to tout their brilliance and insist their success is inevitable.


Hope you enjoyed my screed!


Am I missing any other red flags?

🎈 Mentorship
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🧠 Advice
73
funcoupons
WR Officer
19
👑
Great post! Startups often do a fantastic job at selling naïve salespeople a big shiny dream but can't seem to pull it together when it comes to selling themselves and their products to investors/potential clients. You make some super important points.
braintank
Politicker
8
Enterprise Account Executive
Thanks! Admittedly, I learned a TON working at failing startups early in my career (i.e. don't do these things). However now that I have a family and mortgage, I can't afford to take the risk. Moreover, with the market for talent as hot as it is right now, there's no sense toiling away at a spot destined to fail.
funcoupons
WR Officer
10
👑
Yeah, it scares me when I read about people who also have families and major financial commitments considering jumping ship from a well established company to a brand new startup... When you're fresh out of college with only a cell phone bill and beer money to worry about you can afford to take the risk, but when you're a real established adult you need to be REALLY confident that it's going to work out before you make any decisions.
TheNegotiator
Arsonist
7
VP of Sales
This is where I am now, and my company is a TRAINWRECK that fell out of a nuclear tsunami.
.
I am their only lifeline, and for that they gave me a 177% increase in Base and a 250% on OTE, 5 weeks off and options. So, I’ll make it work
funcoupons
WR Officer
3
👑
Sounds like their failure is your success. It be like that sometimes.
SADNESSLieutenant
Politicker
2
Officer of ♥️
me wishing I read this post 2 months ago
hh456
Celebrated Contributor
13
sales
Start ups aren't for everyone. I always took start up jobs just because I had a chance to make it work. I was also young (usually) could live off the snacks at the kitchen and they didn't interfere with my esports outside of work.

Once I got used to living on a more lean budget I just stayed in the space, lots of upside if you have the stomach for it. But don't do it if you're comfy, have a mortgage, kids, debt, etc. It's not a wise choice.

I love it, wouldn't have it any other way. So glad I didn't go corporate.
poweredbycaffeine
WR Lieutenant
9
☕️
When I think of toxicity, I think of culture and leadership--so #4 on your list hit the nail on the head for me.
braintank
Politicker
5
Enterprise Account Executive
True -- maybe "toxic" isn't the best headline. 
poweredbycaffeine
WR Lieutenant
8
☕️
"How to avoid a dumpster fire" is pretty spot-on for the post you wrote. Very well done, btw.
braintank
Politicker
5
Enterprise Account Executive
LoL - when you're cold enough even a dumpster fire looks enticing... 
ColdCallFartBoy
Celebrated Contributor
1
Business Development Representative
Absolutely hits home for me as well
JohnnyDamone
Opinionated
0
AE Inside Sales
I worked at a great startup that had a great product and great reviews. Culture was crappy. SDRs got fired because there weren't enough leads, and AE's were forced to take crappy leads to make sure people don't get fired. Love the co-workers, hated the culture. Sucks because the colleagues rocked. 
pwnzor
Opinionated
0
Head of Sales
This sounds precisely like a few of the startups friends have worked at and similar to the one I work at now, although we are succeeding despite ourselves at the moment.
Beans
Big Shot
8
Enterprise Account Executive
Love the high quality content.

Point 1 is what so many people fall for, that spending of "fake it til you make it" is a death knell for most newcomers. 
braintank
Politicker
6
Enterprise Account Executive
100% 

Better off working out of a garage and being cash-flow positive than working from a swanky converted warehouse with nap pods and espresso machines and burning through cash.

But, it's a lot easier to get people to sign offer letters if the office is plush.
UrAssIsSaaS
Arsonist
3
SaaS Eater
Just WFH and you eliminate all of these issues. I know it creates others but just saying 
Champagnemami
Executive
1
AE
love wfh
CuriousFox
WR Officer
6
🦊
Another spot on post with actual helpful guidance and advice. Bravo. 
InQ5WeTrust
Arsonist
6
No marketing, mayo isn't an MQL
As a member of previously doomed startups, I endorse this messaging. 
thatsaleswoman
Member
0
Enterprise Account Executive
I endorse this message
Sunbunny31
Politicker
5
Sr Sales Executive 🐰
This is a great post.   I worked for a company that failed in the dotcom bust  and watched our offices shrink to a couple of desks with the rest of the floors subcontracted.  It was painful.  My next startup was acquired.   This whole post resonated.

The difference between 01 and now is that it's a sales rep's market, so there's no need to hang out when the lights are slowly going out.
braintank
Politicker
6
Enterprise Account Executive
That's exactly where I'm at. Gave my new venture 90 days. Red flags continued to mount. Asked myself: is it worth staying around trying to fix things that can't be fixed (i.e. CEO's hubris)? Answer was a clear "no". Tapped my network and I had 3 offers in 30 days.
Sunbunny31
Politicker
2
Sr Sales Executive 🐰
That's great!   I wouldn't wish the hiring environment of late 01/all of 02 on anyone.  This is good news.
UrAssIsSaaS
Arsonist
4
SaaS Eater
Appreciate the shoutout and glad it inspired you because this is some HEAT! Spot on throughout the entire list. 

#1 is such a simple one to ID idk why more people dont see it. No chance Im moving to a company that has a sick office but no path to sustained revenue. 
IanJ
Executive
4
Enterprise Business Development
Avoid start ups with family members high up in the start up.

CTO and COO are the founder's siblings?

Byeeeee! 
JohnnyDamone
Opinionated
0
AE Inside Sales
what about if the CEO is the teacher and the founding members are all students LOL???
goldenlazard
Politicker
0
Senior SDR
then you've joined a cult haha

ever seen Dan Lok's videos?
braintank
Politicker
3
Enterprise Account Executive
Thought of another one: co-CEOs. If you see this, run!
bandabanda
Tycoon
3
Senior AE Mid Market
This is flames!! Point 4 is SOooo spot on. I'm working at a Series A startup right now and we're doing well, but number 4 reminded me A LOT of our founder. That's the biggest crack I see in our org.

In a SaaS startup, I'd point out red flags if 

- quotas are super aggressive an unattainable. This shows me the CEO and leadership may not quite understand marketing and the board may not be aligned with realistic goals.

- Is the Engineering/Product team being run into the ground to crank out a roadmap that is also too aggressive. Additionally, before releasing a feature, how are they collecting and collating customer feedback to deliver features that users actually want and need. THEN do they move quickly to make changes and improve (there are still parts of our app that make me cringe that have yet to be updated or changed. They actually provide a hint that the product wasn't well thought out in certain areas). I'm all for progress > perfection, but you have to get feedback, analyze, make the feature better, iterate. 

Also died laughing at "hustling 24/7 aint a plan."  Preach!
Diablo
Politicker
2
Sr. AE
Enjoyed reading this. I so much agree with point#2 , so many biz fail because they assume their products are going to solve XYZ problem without having any data to back it.
braintank
Politicker
4
Enterprise Account Executive
100% Good startups build their product alongside potential customers. Even better if they realized their product demand at their previous job (e.g. I was working at X and realized despite our resources we couldn't do Y).

Doomed startups build their product in a conference room vacuum. The fumes from dry erase markers make them think they're geniuses. 
Jewcan_Sam81
Politicker
2
Account Executive
Really feel that there are so many startups that I refer to as "Techquity Startups" because they sell on this dream that they're the next big thing, but most of the time it's run by people as clueless as the people they bring into their vision. 

I feel like people are churned and burned in places like that by people that just make a grip of money and then peace out to the next thing.

The big sales orgs at big corporations might seem like a drag, but still a better bet
braintank
Politicker
4
Enterprise Account Executive
Great points! Always search on LinkedIn for "past not current" employees. If the count seems high compared to the size of the org that's a red flag.

As for big sales orgs -- they got big for a reason! 
Champagnemami
Executive
1
AE
oooh thats a good tip to see past employees compared to current employee count! 

when you said big sales orgs got big for a reason, can you expand on that? not sure if you mean it in a good or bad way
UrAssIsSaaS
Arsonist
3
SaaS Eater
I think "better bet" is very subjective. They are certainly a "safer" bet but a lot of that comes down to risk tolerance and what someone is looking for in their career. 

A 22 year old out of college only has to worry about rent and drinking money. They can afford to take a risk w/ a high upside role. However a 35 year old parent of 2 with a house and 2 cars has to views these things differently. 
Jewcan_Sam81
Politicker
3
Account Executive
This is a good point actually. Safer bet is probably better way to put it, and it really just depends on age, career path progress, etc. Good call
Mobi85
Politicker
2
Regional Sales Manager
Thank you for the spot on post and insight into startups
Extrabutteredup
Opinionated
2
Producer
1. Check, 2. Yup, 3. Uh huh, 4. Oh come on! Everything in this post brought back painful flashbacks. If only I read it before I was a naive young sales lad. Great Post. 
IanJ
Executive
2
Enterprise Business Development
If they repeatedly talk about foosball tables and snacks. Especially if they talk about that more than product roadmap, departmental plans, recent wins, etc...
DungeonsNDemos
Big Shot
1
Rolling 20's all day
#4 gave me flashbacks to the last place I worked haha. Spot on with your analysis! Great post
ventox35
Politicker
1
Sales Leader
Good stuff! I think you can make it work if you check at least 2 or 3 of those boxes. for instance: you can somewhat adapt the product to fit what the market needs. sometimes it takes a crappy product at first for you to realize you need a not crappy product-so you adapt. bootstrapping is tough as heck, but often necessary-you can overcome with a solid foundational client base. shaky business model? good luck overcoming that! ceo too stubborn to let go of control of "my baby?" good luck with that! #4 is probably the most important. gotta have the right people. want to know if they're the right people? challenge their product and business model when you meet with them. see how they react.


braintank
Politicker
4
Enterprise Account Executive
Agreed -- no startup is perfect. You can add features or adjust GTM strategy, but if leadership is toxic that can't be changed. I approach interviewing at startups with the mindset of an investor. Would I be willing to write these people at 7-figure check? If not, then move on. 
ZeroGrit
Valued Contributor
1
VP of Hoping My Emails Find You Well
This is a fire post.
braintank
Politicker
4
Enterprise Account Executive
If I can prevent one 25-year-old from burning themselves out and moving back in with their parents because of the promise of unlimited PTO, endless kombucha, and a game room with a VR headset it'll all be worth it...
cw95
Politicker
1
Sales Development Lead
From experience, never truly trust what the ceo says in terms of liquidity.
Justatitle
Big Shot
1
Account Executive
very solid post and some great advice in here
Mjollnir
Politicker
1
Account Executive
This is a great post.
Just had an interview with a small start up, and I'm sure to include follow up questions in my next interview!
yomamasofat
Good Citizen
0
manager
good luck!
IanJ
Executive
1
Enterprise Business Development
Founders or CEO who isn't selling or promoting the company all the time. 

Context, our CEO made his first post about the company in  7 months on LinkedIn this week.
4 co-founders and only 1 is actively helping on sales calls and engaging in related Slack communities and on LinkedIn, etc. 
BentoBri
Executive
1
Senior AE
Great points and I couldn't agree more.  We're a well funded seed stage startup (lol @ well funded at seed stage) and our adoption has been well below expectations.  However, no one besides I (responsible for selling our platform to one vertical) seems worried! I'm looking to jump ship specifically because of points 2 and 3.  Great team, just don't think the product is there.  I come from an untraditional sales background as I was a financial advisor of sorts that transitioned into a "Head of Sales" role at a fintech startup.  Trying to figure out how to pivot into other fintech sales but the required experience seems out of reach while a junior level sales role seems, well, too junior.  Any advice or mentors would be greatly appreciated.  Not sure this is the place to post!
Champagnemami
Executive
1
AE
thank you so much for this!
Lioness
Good Citizen
1
Sr Field Enterprise Account Executive
Good advice! I'd say also inquire into how the company is defining "customer." Unpaid users aren't customers. Pilots that don't convert aren't customers. 
braintank
Politicker
1
Enterprise Account Executive
The company that inspired this post had massive layoffs today.
Salesify
Executive
0
AE
Great post! Sounds crazy, but depending on the size, being “too ambitious” can be a red flag. My last one tried to take over the end to end workflow of its space but just ended up spreading itself too thin. The core product was forgotten about and competitors went to town!
Espo
Personal Narrative
0
General Sales Manager
Bells went off in my head as I read your post. You can't be more spot on with your reflections on the perils of selling for a startup. You also gave me a great set of answers for my next interview when they ask me, "tell me about your last job, why did you leave?"
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