In November and December of 2025, I reached out to a business broker about buying a bar. I signed a nondisclosure agreement and was given access to their financial records. The bar was being sold for about $70k. What that $70k bought you was the existing lease (which would have to be renegotiated within a year), the liquor license (a limited license for beer and wine worth about $2k), and the furniture, fixtures, and equipment. At the time, the bar was operating as an Amy Winehouse themed wine bar. It used Winehouse as part of it’s name – get it? wine house. The financials weren’t great – it was losing about $15k per year, but those losses seemed entirely fixable.
When I visited, they had about 8 or 9 customers come through in about an hour or two, they sold mostly wine, a hot chocolate concoction, and a few bottles of beer (mostly to me) – their six draft beer lines needed to be serviced. Among the “problems” I identified: they were only open 20 hours per week (Thur, Fri, Sat); they were charging a cover two nights a week; and the house band for one of those nights was usually an Amy Winehouse cover band (the owner was the singer). Changing any one of those things, seemed like it would be enough to put the business in the black. Changing all four seemed like a no-brainer, easy fix. Be open more days and longer hours, don’t charge a cover fee, bring in different music, and get the taps flowing. As I was reading up on how to form an LLC and how to get a business loan (a chicken and egg problem that paralyzes a newbie like me), someone else bought the bar. It wasn’t until buying was no longer an option that I realized how invested I had become in the idea. Now when I walk by, I see that it seems to be doing well (or at least better), they have longer hours, and I think about what could have been. I coulda been a contender.
A little over a month ago, I signed another nondisclosure and expressed interest in another bar. The asking price is higher, and the financials a little more “complicated” (I can’t really say anything detailed because it hasn’t sold and I signed a nondisclosure). The appeal, for me, is that it’s an old-school, institution type of business. It’s been around for over a century and is mentioned in a few different books. It’s appeared in movies, and famous musicians and comedians have performed there (Robin Williams, Guns and Roses, and others). It’s a small and intimate space. One of its weekly events is the longest running event of its kind in the city.
I visited the bar twice on two different nights. The location is a challenge. Situated near a major intersection with on- and off-ramps to the highway, it’s not exactly walker friendly (though there are crosswalks). Moreover, there’s not a lot going on in the neighborhood – it used to be more industrial. That said, the neighborhood could be described as up and coming. There are a few new apartment buildings with more development on the way.
I’ve reviewed three years of financial records and made multiple attempts to “break apart” their profit and loss statements. By break apart, I mean run different scenarios of growth or losses, different scenarios in which I cut staffing costs by taking on some of the labor, different scenarios in which I split the business in two by forming a cultural nonprofit to absorb some rent and assume all of cost and responsibilities associated with the music/art side of the business. None of my simulations deliver the results I want, and even the purchase price would require me to raise funds, dip into retirement, and/or take loans, etc. – which means I probably have to pass.
Having twice gone through the process of evaluating bars for sale, I find myself asking some fundamental questions like, why do I want to buy a bar? and being frustrated by the reality that, risk is easier when you have lots of money to lose… the extremely wealthy don’t seem to care about losing vast sums of money. I am not even remotely wealthy.
Why a bar?
Ever since running lemonade stands as a kid and a car-washing “business” as a pre-teen, I’ve had a slight entrepreneurial streak. While other kids played video games like Zelda and Mario Bros., I spent my time playing business and management simulation games (Project Space Station, Aerobiz, Sim City, Railroad Tycoon, Capitalism). It is, admittedly, an odd interest for someone who claims to be an anti-capitalist. It’s true, I’m not a fan of capitalism, but I am very much in favor of small business. I see the small business operator as someone who identifies a community need and then tries to meet that need with their particular skill set: bakers, tailors, artisans, etc. To me, the impetus behind most small businesses isn’t to get wildly wealthy, but is to earn a living while meeting a community need and doing something that they’re good at and enjoy. In this respect, it’s not terribly different from a grassroots nonprofit. I’ve been running nonprofits for years.
As for the why a bar as opposed to other businesses – it’s a combination of interest and skill (or lack thereof). I spend a fair amount of time in bars. I like that they’re places where people from different backgrounds come together. I like that the good ones build a sense of community. Third spaces (those places that aren’t work and aren’t home) play an important role in society. Moreover, as social media and our digital worlds continue to divide us, I believe third spaces where we can gather in person will become increasingly valuable (at least for those who want them). There is a palpable sense that at least some, if not a significant part, of the population wants better and more meaningful connections with their community. Bars have a role in that space. As for the skills (or lack thereof) – I have no culinary skills or baking skills so restaurants and bakeries are off the table; I’m not mechanically inclined and won’t be running an auto repair shop or home repair business; I have no fashion sense and won’t be running a boutique store; I like books, but bookstores are a tough business (I worked in one for several years) and San Francisco already has a lot of good bookstores. I can talk to people, I’m reasonably good at building community, and I have a slight preference for beer over coffee (and there are better margins on liquor). A bar, for me, makes sense.
There are other less tangible or quantifiable reasons for why I’d like to get in to the bar business. For a long time, I’ve been saying I want off the ride or want to be on a different ride. I define the ride as the typical 9 – 5 grind, the meetings, the posturing, the office politics. I’m fortunate that I don’t have much of that in my current job, but my current job (part-time) is not financially sustainable. I need something else. When I look for something else, there are very few things that get me excited. I apply to the ones that do (usually in the arts or business development field), but there are a lot more nonprofit jobs where I’m probably qualified, but unmotivated. And because much of the nonprofit sector has shifted towards courting family philanthropy from organizations with wealth of dubious origins (tech oligarchs, oil money, etc.) I’m finding myself less willing to compromise my ethics for a buck. Moreover, in the job market, especially during the interviews, you have to show that you’re emphatically, swooningly in love with them – and well, I’m old and tired of playing that game. It’s a job, not a wedding proposal. It’s not ’till death do us part – we’ll probably, at some point, part. Beyond those things, I’m tired of the constant threat of technological disruption. I want something simpler, more straightforward. A bar, while they have their complications, seems simpler and more straightforward.
I recognize that one shouldn’t base their avocation solely on what they don’t want to do… On the positive side of the ledger, building things excites me and I have a reasonable network of support. One of the best experiences of my life was when I started my own literary journal. I didn’t know what I was doing and had a blast learning and trying, succeeding and failing. Generally speaking, I’m risk averse, but some of the most memorable times in my life have been when I’ve taken risks. Many years ago when I left my job to do consulting work, I became tangentially immersed in the New York literary scene. I had gotten phone calls from Henry Louis Gates, Jr. and had attended a fundraiser for The Paris Review where Mayor Bloomberg was a guest as were Salman Rushdie, Moby, E.L. Doctorow, and others. Much more recently, I took a gamble and moved to California – the two-month road trip around the country was one of the best bets I’ve ever made on myself. As for the network of support, most of my friends in San Francisco are bartenders or servers. As such, I have a ton of people whose expertise could guide me. Moreover, most of them have said I’d make a great bartender/owner because I’m patient, attentive, and easy to get along with. Back when I thought about buying the wine bar, one of my friends (who is in the wine business) said he’d help me source product while another friend (a bartender) said he’d do a walk through to help me create a punch list of what needs to be fixed. After sharing with my brother that I almost bought a bar, he said I should talk to him next time – he might want to invest. A long-time friend in living in LA has said the same thing, he’s got some money he could put in. Meanwhile, my daughter has said she thinks I’d be a natural in the business.
Barriers, Fear, and Frustration
The biggest barrier for any of these endeavors is capital. I don’t have a pile of cash to burn. I’d have to take out loans, and depending on price, I’d probably have to tap into my retirement. The cynic in me has a pretty negative outlook about the state of our economy. As such, I figure my retirement is already at risk. The way I see it, we’re in a bubble that’s going to burst and my retirement, along with countless others, will vanish. This leaves me asking, “why am I gambling on a tech bubble over which I have no control and from which I can’t easily divest when I could gamble on myself?”
The next biggest barrier is fear. What if it doesn’t work out? That fear leads to over-analysis and over-thinking. While I overthought the wine bar, someone jumped in and bought it. Time will tell if that was a mistake on my part. My intuition on the current bar says it would be harder to turn around… but it’s also the type of thing you can’t really know until you’re in it.
That’s where the frustration comes in. I live in San Francisco. People dream big here. They take risks. Moreover, there’s lots of “fuck you” money floating around. In a recent book that I read, a billionaire investor easily wrote off a $150M investment to simply buy out an under-performing business partner – they were friends. With deep pockets comes greater tolerance for risk. It’s difficult for me to square some people’s willingness to lose millions of dollars on bad investments while I’m worried about a few hundred thousand (an by few, I mean more than 2 and less than 5) on an untested investment that has managed to stay in business for over a century. Amazon lost money for eight to nine years before it ever turned a profit. And while a bar is no Amazon, I would love to have a one-year runway to experiment and turn things around.
What’s Next
I’ve waffled back and forth on this thing. The waffling could be seen as a good reason to not go for it. The fact that I keep coming back to it could be seen as a good reason to go for it. In such situations, I usually wait until a more clear decision presents itself to me or is made for me.
When I talk to friends, most of them want me to go for it. Some will say, maybe not this one, but something else might come up. Last week, while standing in line for a free concert hosted by the band Train, I talked with a woman about living in the city and the cool bars and everything. [Side note: Train was playing a free show outside of the bar that gave them their first paying gig… bars are places where history is made.] I mentioned that I was looking at buying a bar and when I told her which one, she told me that she works for the city in their department of economic development and there are people who would like to see me succeed at such an endeavor. She proceeded to give me the names and email addresses of her colleagues who might be able to help. I’m tempted, but I also don’t want to waste anyone’s time.
Without a clear next step and far too much trepidation to jump in with both feet, I suppose I’ll wait it out. Waiting it out means finding other work – some of which excites me, some of which doesn’t. Waiting it out means getting my own finances in better shape so that should another opportunity pop up, I might be less risk averse. Waiting it out also means being open (though not necessarily hopeful) that other circumstances might change (still waiting on that sugar mama) – preferably before the AI bubble bursts and takes us all with it. In the mean time, I’ll continue to observe my bartender friends, study the economics of the city, and contemplate life as publican (bar owner).