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I was basically alone. I didn’t have a team, nor an office. And San Francisco was full of startups raising gobs more money, building amazing teams, and shipping

I was basically alone. I didn’t have a team, nor an office. And San Francisco was full of startups raising gobs more money, building amazing teams, and shipping great products. Some of my friends became billionaires. Meanwhile, I had to run a “measly” lifestyle business. It wasn’t what I wanted to do, but I had to keep the ship from sinking. There's that term again, "lifestyle business." Uttered like a dirty word, when in fact Sahil has an actual product that many thousands of people use and pay for. I'm one of them. Meanwhile, many startups aren’t true businesses – they book no revenue, and they may not even have a sellable product. That’s fine, because almost all businesses start with an idea or a dream or a need or pure desperation, and it’s up to the founders to make it work. They may even need investment, too – sometimes a lot of it. And that’s fine, too. But when people from the startup world use the term “lifestyle business” to describe real businesses that aren’t pure tech, have solo founders, don’t take VC money, don’t intend to scale to a billion users, or whatever other qualities are not worthy of investor consideration, I find it condescending and misguided. Some startups could actually learn a thing or two from the vendor who sells hot dogs in the park, the person who starts up a specialist marketing agency, the partnership that builds a ceramics factory, or the solo founder running a media distribution and sales platform. They have products or services to sell. They have customers. They book revenue, pay their employees and suppliers, and if they do things right, may even become really successful. In short, people who run small businesses are not hobbyists or dilettantes. They’re entrepreneurs doing real business selling something, often with limited capital and without the glamor or hype. Kudos to Sahil for what he's accomplished. But for the love of Pete, please stop using the term "lifestyle business."

keerthiko 8y ago
I think this comment is an unfair treatment of Sahil's opinion. He disclaimers all this at the start with the following: > Now, it may look like I am in an enviable position, running a profitable, growing, and low-maintenance software business with customers who adore us. But for years, I considered myself a failure. At my lowest point, I had to lay off 75% of my company, including many of my best friends. I had failed. > I no longer feel shame in the path I took to get to where I am today. It took me years to realize that I was misguided from the outset. This is that journey, from the beginning. He acknowledges that he is grateful and proud of his lifestyle business. There's nothing wrong with the phrase itself. I run a lifestyle tech business as well. I'm proud of it. I switch between "small business", "sustainable long-term business" and "lifestyle business" depending on my audience. "lifestyle business" doesn't have to be a dirty word if you don't use it as one.
rdiddly 8y ago
Isn't it just a VC term that has snuck into the vernacular? As builders and creators of value, we do ourselves a disservice by using the same language as that used by those who only deploy value - or more accurately who rent it out opportunistically - and have different values and priorities.
Swizec 8y ago
I also use Gumroad and also used to think lifestyle business is bad. But really it just means “business that supports a lifestyle”. Which a “startup” does not. In that light, startup is the bad word when you think about it. What, you run a business that can’t even support your lifestyle? LooooooL And yes if I’ve learned anything about silicon valkey in the past 4 years of living here is that people are elitist as fuck, hate their lives, and grab onto any little thing to make themselves feel better than others. It’s what they need to endure the grind and that’s okay. I get it.
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aeden 8y ago
I agree 100%. I'm a big fan of just calling them businesses.
graeme 8y ago
He's talking about switching from vc rocketship to bootstrapped. In that context the pejorative makes sense: he's describing how he felt at the time. Furthes, he ran this "lifestyle" business with outside investors. He's written a nuanced, heartfelt essay, and this comment seems to have missed all of that to nitpick on a word.
- jstandard 8y ago
  Agree the essay was a great read. I didn't see anything to suggest the OP missed that fact so much as had a reaction to a specific part of the essay and wished to discuss it. Being a part of the SV startup ecosystem myself, I also see the term "lifestyle business" used as a soft-perjorative for "not ambitious enough".
  - graeme 8y ago
    That's exactly how OP was using it though, with full awareness. OP's mindset at the time was "I failed: I meant to start a billion dollar business, and I only have a crummy lifestyle business" They now have come around and appreciate their success. Their use of "lifestyle business" was chosen to convey their own negative attitude at the time. The comment I replied to totally missed that the author wasn't critcizing their own business! They just felt badly about it a few years ago. See the part of the comment where they praise gumroad. A more self aware comment would have merely decried the prevailing VC attitude that led the founder to feel bad. Instead the commentor seems to think the founder needs cheering up and convincing.
    - jstandard 8y ago
      I see your point. The admonishment to Sahil at the end to "stop using" the term "lifestyle business" does seem to miss Sahil's self-awareness of the internal conflict between knowing about the misuse of the term and yet still allowing it to affect him at one point in time. It's refreshing to see this perspective from founders. It's a story not often told and does well to characterize the grinding rollercoaster of hard decisions you won't easily find in the sea of "A-co raised $40mm!" press releases.
eeeeeeeeeeeee 8y ago
I also found it illuminating how quickly the investors wanted to just dump the entire thing, which would have almost certainly left all the businesses in the lurch, like we see with so many companies these days, especially in the valley. People seem to forget that the VCs are hidden from the blowback of those cut-and-run decisions, so it's easy for them to make those flippant recommendations. It is the executives who will be publicly shamed for cutting and running and that reputation will follow them and likely catch up to them. Good on Sahil for sticking it through and getting out of the bubble and realizing that chasing money is not the path to happiness.
billylindeman 8y ago
Couldn't agree more. The lack of business sense in the startup scene is absolutely astounding. Too many opt for playing game of thrones instead of creating value and capturing some of that value as a profit.
dbt00 8y ago
Most people use the term to describe businesses that require little ongoing effort (hello, “4 hour work week”), but yeah, the implication that people who take vc money aren’t interested in a particular lifestyle is kinda hilarious.
Justsignedup 8y ago
"lifestyle business" is really just a small business that works, is self-sustaining, and not overly bloated to attempt to make obscene amounts of $$$. I feel like this is exactly what most companies should strive for. They'll make better decisions that way.
- trhway 8y ago
  >"lifestyle business" is really just a small business that works, is self-sustaining, and not overly bloated to attempt to make obscene amounts of $$$. I guess it sounds too bourgeois for the young (and not so) SV rebels who are in to change the world and make some billions along the way.
- ian0 8y ago
  Isnt a "lifestyle" business a business to support the lifestyle of the founder? IE money is not typically a problem, either the company is profitable or the founder will support it loss making. The main function of the company is to keep the founder entertained more than anything else. There are a lot of companies like this (big & small), though sometimes its not recognisable from the outside. Note the goal is still ostensibly to make money. You don't run a business when you could have retired if you don't love growing businesses. I cant imagine a founder turning down an offer to expand rapidly, if it made sense. They just tend to avoiding going all in on a particular bet and for obvious reasons don't like ceeding control to outside investors.
  - pandapower2 8y ago
    >Isnt a "lifestyle" business a business to support the lifestyle of the founder? IE money is not typically a problem, either the company is profitable or the founder will support it loss making. The main function of the company is to keep the founder entertained more than anything else. I don't think I've heard the phrase lifestyle business used that way. I'm not in the US let alone silicon valley so that might be relevant. Rather I've heard lifestyle business used to describe a business, typically with zero to half a dozen employees, which the founder can run without putting in a whole bunch of time. A real but deliberately vague example. A company that acts as an authorized dealer for a manufacturer. The sales company handles the sales process and takes orders through a website supplemented with phone calls. Actually shipping the merchandise and handling after sales customer support is done by the manufacturer. Why they don't want to do their own sales I don't know. Staffing requirements are one person to answer any phone calls and someone to do the books. Owner's required time is maybe a few hours a day. Commissions on sales cover all the bills etc and let the owner pay themselves handsomely but it will never be a giant enterprise.
michaelbuckbee 8y ago
I like and use the term "Bootstrapped Business" -> smaller, tight focus on profitability, trying to meet real needs.
- mikeg8 8y ago
  I agree and use it sometimes too but hearing "bootstrapped" applied to companies outside of tech doesn't feel right. Example: my dad owns a 20 person small business selling commercial doors and hardware - we are in the construction industry. Saying he has "bootstrapped the business" still feels weird. That's when good old "small business" should be sufficient enough IMO. It has a stigma but it shouldn't.
  - michaelbuckbee 8y ago
    Yeah, I mean I guess there are more qualifiers I didn't put in there with respect to tech: "Bootstrapped Software Business", "Bootstrapped SAAS", etc.
austincheney 8y ago
Worse than the use of the term lifestyle business is his definition of success. Success is his placement relative to other people who become billionaires. He describes this several times. That is vanity rather than any sort of imperative or objective goal describing a business position. To me vanity is a major red flag. That sort of self serving quality needs to describe the founder as somebody willing to ask for cash and drive necessary growth, but must not be a goal driving the business. The difference is that the qualities (appearance) of vanity are attainable early.

keerthiko 8y ago

I think this comment is an unfair treatment of Sahil's opinion. He disclaimers all this at the start with the following: > Now, it may look like I am in an enviable position, running a profitable, growing, and low-maintenance software business with customers who adore us. But for years, I considered myself a failure. At my lowest point, I had to lay off 75% of my company, including many of my best friends. I had failed. > I no longer feel shame in the path I took to get to where I am today. It took me years to realize that I was misguided from the outset. This is that journey, from the beginning. He acknowledges that he is grateful and proud of his lifestyle business. There's nothing wrong with the phrase itself. I run a lifestyle tech business as well. I'm proud of it. I switch between "small business", "sustainable long-term business" and "lifestyle business" depending on my audience. "lifestyle business" doesn't have to be a dirty word if you don't use it as one.

rdiddly 8y ago

Isn't it just a VC term that has snuck into the vernacular? As builders and creators of value, we do ourselves a disservice by using the same language as that used by those who only deploy value - or more accurately who rent it out opportunistically - and have different values and priorities.

Swizec 8y ago

I also use Gumroad and also used to think lifestyle business is bad. But really it just means “business that supports a lifestyle”. Which a “startup” does not. In that light, startup is the bad word when you think about it. What, you run a business that can’t even support your lifestyle? LooooooL And yes if I’ve learned anything about silicon valkey in the past 4 years of living here is that people are elitist as fuck, hate their lives, and grab onto any little thing to make themselves feel better than others. It’s what they need to endure the grind and that’s okay. I get it.

deleted 8y ago
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aeden 8y ago

I agree 100%. I'm a big fan of just calling them businesses.

graeme 8y ago

He's talking about switching from vc rocketship to bootstrapped. In that context the pejorative makes sense: he's describing how he felt at the time. Furthes, he ran this "lifestyle" business with outside investors. He's written a nuanced, heartfelt essay, and this comment seems to have missed all of that to nitpick on a word.

jstandard 8y ago
Agree the essay was a great read. I didn't see anything to suggest the OP missed that fact so much as had a reaction to a specific part of the essay and wished to discuss it. Being a part of the SV startup ecosystem myself, I also see the term "lifestyle business" used as a soft-perjorative for "not ambitious enough".
- graeme 8y ago
  That's exactly how OP was using it though, with full awareness. OP's mindset at the time was "I failed: I meant to start a billion dollar business, and I only have a crummy lifestyle business" They now have come around and appreciate their success. Their use of "lifestyle business" was chosen to convey their own negative attitude at the time. The comment I replied to totally missed that the author wasn't critcizing their own business! They just felt badly about it a few years ago. See the part of the comment where they praise gumroad. A more self aware comment would have merely decried the prevailing VC attitude that led the founder to feel bad. Instead the commentor seems to think the founder needs cheering up and convincing.
  - jstandard 8y ago
    I see your point. The admonishment to Sahil at the end to "stop using" the term "lifestyle business" does seem to miss Sahil's self-awareness of the internal conflict between knowing about the misuse of the term and yet still allowing it to affect him at one point in time. It's refreshing to see this perspective from founders. It's a story not often told and does well to characterize the grinding rollercoaster of hard decisions you won't easily find in the sea of "A-co raised $40mm!" press releases.

eeeeeeeeeeeee 8y ago

I also found it illuminating how quickly the investors wanted to just dump the entire thing, which would have almost certainly left all the businesses in the lurch, like we see with so many companies these days, especially in the valley. People seem to forget that the VCs are hidden from the blowback of those cut-and-run decisions, so it's easy for them to make those flippant recommendations. It is the executives who will be publicly shamed for cutting and running and that reputation will follow them and likely catch up to them. Good on Sahil for sticking it through and getting out of the bubble and realizing that chasing money is not the path to happiness.

billylindeman 8y ago

Couldn't agree more. The lack of business sense in the startup scene is absolutely astounding. Too many opt for playing game of thrones instead of creating value and capturing some of that value as a profit.

dbt00 8y ago

Most people use the term to describe businesses that require little ongoing effort (hello, “4 hour work week”), but yeah, the implication that people who take vc money aren’t interested in a particular lifestyle is kinda hilarious.

Justsignedup 8y ago

"lifestyle business" is really just a small business that works, is self-sustaining, and not overly bloated to attempt to make obscene amounts of $$$. I feel like this is exactly what most companies should strive for. They'll make better decisions that way.

trhway 8y ago
>"lifestyle business" is really just a small business that works, is self-sustaining, and not overly bloated to attempt to make obscene amounts of $$$. I guess it sounds too bourgeois for the young (and not so) SV rebels who are in to change the world and make some billions along the way.
ian0 8y ago
Isnt a "lifestyle" business a business to support the lifestyle of the founder? IE money is not typically a problem, either the company is profitable or the founder will support it loss making. The main function of the company is to keep the founder entertained more than anything else. There are a lot of companies like this (big & small), though sometimes its not recognisable from the outside. Note the goal is still ostensibly to make money. You don't run a business when you could have retired if you don't love growing businesses. I cant imagine a founder turning down an offer to expand rapidly, if it made sense. They just tend to avoiding going all in on a particular bet and for obvious reasons don't like ceeding control to outside investors.
- pandapower2 8y ago
  >Isnt a "lifestyle" business a business to support the lifestyle of the founder? IE money is not typically a problem, either the company is profitable or the founder will support it loss making. The main function of the company is to keep the founder entertained more than anything else. I don't think I've heard the phrase lifestyle business used that way. I'm not in the US let alone silicon valley so that might be relevant. Rather I've heard lifestyle business used to describe a business, typically with zero to half a dozen employees, which the founder can run without putting in a whole bunch of time. A real but deliberately vague example. A company that acts as an authorized dealer for a manufacturer. The sales company handles the sales process and takes orders through a website supplemented with phone calls. Actually shipping the merchandise and handling after sales customer support is done by the manufacturer. Why they don't want to do their own sales I don't know. Staffing requirements are one person to answer any phone calls and someone to do the books. Owner's required time is maybe a few hours a day. Commissions on sales cover all the bills etc and let the owner pay themselves handsomely but it will never be a giant enterprise.

michaelbuckbee 8y ago

I like and use the term "Bootstrapped Business" -> smaller, tight focus on profitability, trying to meet real needs.

mikeg8 8y ago
I agree and use it sometimes too but hearing "bootstrapped" applied to companies outside of tech doesn't feel right. Example: my dad owns a 20 person small business selling commercial doors and hardware - we are in the construction industry. Saying he has "bootstrapped the business" still feels weird. That's when good old "small business" should be sufficient enough IMO. It has a stigma but it shouldn't.
- michaelbuckbee 8y ago
  Yeah, I mean I guess there are more qualifiers I didn't put in there with respect to tech: "Bootstrapped Software Business", "Bootstrapped SAAS", etc.

austincheney 8y ago

Worse than the use of the term lifestyle business is his definition of success. Success is his placement relative to other people who become billionaires. He describes this several times. That is vanity rather than any sort of imperative or objective goal describing a business position. To me vanity is a major red flag. That sort of self serving quality needs to describe the founder as somebody willing to ask for cash and drive necessary growth, but must not be a goal driving the business. The difference is that the qualities (appearance) of vanity are attainable early.