THEN and NOW: @WallStreetOasis.com

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Inspired by the recent return of some all-time great WSO members, we will begin featuring a series of posts from forum favorite 'superusers'. This "Then and Now" series will let people share a bit of their story through a handful of questions that touch on their career progression and how this site has supported that.

Expect posts over the next couple weeks from CompBanker , thebrofessor , Frieds , APAE , brotherbear , Layne Staley , CRE , IlliniProgrammer , and if we're lucky, even Eddie Braverman

When did you first join WSO?
May 2006

Why did you join?
I founded the community and thought it would be a fun place for younger investment bankers and prospective investment bankers to discuss careers and shoot the shit.

Where were you in your career then?
In 2006 I was working in private equity at Tailwind Capital in New York. I had been fired the previous year from a PE fund in Boston called Heritage Partners and was still a bit rattled but was lucky enough to land on my feet after ~4 months of being unemployed.

By the time the 2008 financial crisis rolled around, I was already in business school and so focused on WSO that it luckily didn't impact me directly ...it was like I was insulated in 2 bubbles (Wharton + not recruiting for finance anymore) that made it more like a movie than real life...I have to say 2020 feels eerily similar (I'm here working from home which hasn't changed anything for me except that now I have 3 screaming kids at home all day instead of part of the day).

Where are you in your career now?
Since getting my MBA from Wharton in 2010, it’s been full time WSO for almost a decade! We have some exciting plans for the back half of this year and some major investments going on for the back end that should put us in great shape for 2021 and beyond.

What can you share about your personal or family life?
I had been single while in Boston but had a girlfriend soon after moving back to New York in 2005... but the idea of a wife and kids seemed super far off. I ended up working at Tailwind for almost 4 years before going for my MBA. I knew by the time I was accepted that I’d be using the 2 year “break” to try and make WSO a real business that could support me.

I was single again midway through my time at Wharton and then all through graduation + my time down in Buenos Aires (where I met AndyLouis at a bar through mutual friends) which was a blast - I ended up staying down in BA for almost a full year.

I moved back to Boston in 2011 and soon after I met my future wife...fast forward to 2020 I’m living out in northern California (South Bay) with her + 3 kids (Every (4), Ronan (2) and Noelle (1)). I feel super blessed to have such an incredible family (both immediate and extended) and we’re trying to look at the positives of this health and economic crisis knowing we are much luckier than most.

Looking back on your career, is there anything that you thought you knew starting out which turned out to be wrong?
Yes. I assumed that if you put your head down and worked hard, everything would take care of itself and I didn’t fully appreciate the importance of building strong connections (both internally and externally at related firms).

While the long hours and hard work happened naturally in banking, I struggled at my first job in private equity. When things went south with the fund, I was fired and dumbstruck. In retrospect, I don’t think I could have prevented that from happening, but if I had had a stronger ally within the firm, I might have been given the inside scoop and understood more what was going on...my network is also what saved my career and got me into Tailwind.

Were there any opportunities that presented themselves along the way that you didn't take? With the benefit of hindsight, do you wish you had taken one of them?
I feel like I have run WSO very conservatively and I often second guess whether I should have been more aggressive (maybe working in restructuring made me allergic to debt?). With the benefit of hindsight, nothing dramatically stands out except I should have invested more in design (and a mobile app!) earlier.

Is there anything else you’d like to share?
I think I’d just like to say another thank you to all of the great members that give so much of their time to help others on WSO (many don’t get anything in return except for silver bananas). It’s super motivating when I hear about success stories and I get thank yous from old members that used the platform to learn more and I know this place wouldn’t be anywhere near as useful without the dedication of our top members...so thank you again.

Comments (68)

 
Most Helpful
Apr 7, 2020 - 4:51pm

Patrick, you deserve an immense round of thanks for everything you do to create and maintain this community. I know I'm not the only one who's gotten real value from the people and conversations here. Thank you.

A couple easy questions for you.

  1. How have you scaled this website business? My sense is that you use outsourced dev talent and a few freelance people like Andy to manage the forums.
  2. Have you pursued other online businesses?
  3. How many people have you been able to meet from the forums offline?

Keep it up, we all appreciate you.

I am permanently behind on PMs, it's not personal.

 
Apr 8, 2020 - 11:05am

First off, thanks for the kind words APAE -good to see you back in the forums. I'm hopeful that with a lot of the other superusers around and a concerted effort toward more enlightening discussions that we'll be able to earn you back :-)

How have you scaled this website business? My sense is that you use outsourced dev talent and a few freelance people like Andy to manage the forums.

In terms of staff in the early days (pre 2010) it was really just me and ivyliga as my main assistant and one outsourced developer (she is still with us over 12+ years later - Ivy you rock!). As the site grew and we started bringing in a bit more revenue (it was well under 6 figures for the first 3 years), I was able to build out the team by bringing on jgsantos who has also been with us for 10+ yrs.

Once I moved to Buenos Aires in 2010 I met AndyLouis, and he became the first non-dev hire we made to help me manage the community, newsletters, etc. We've never had hockey stick growth but every year we have been growing revenue steadily (2016 was only flat year) and the team is now closer to ~20 staff (including some all star paid interns) or about ~15 FTEs.

This team as of today includes 5 developers [jgsantos in Brazil, Artem (back end) + Andrey (front end) + Oleksandr (back end) + Alex (mobile dev) in the Ukraine], Ivy (Phillipines) + Bela (Brazil) for customer support + resume and mentor service and Talent Oasis, Hana (toronto) on design, AndyLouis (Mexico city) on social media, community management + newsletters, Matt (toronto) for university partnerships, Nathan (bus dev, AMAs, podcast sourcing) from the UK but living in Thailand, Abbey on socal media support (Phillipines) as well as Daniel and Becca who help with Media editing/production for the podcasts, etc...

More recently I've really tried to bring people on the team that want to work full time on WSO and see us more as a part of their long term vision rather than as a part-time freelance job. I think there is a lot of knowledge and training that we are getting better at systemetizing so that as we grow and bring on more staff it gets easier each time. We even now have a Master Procedure document with a lot of video training :-)

In terms of being able to afford a larger team, it starts with making sure the community is as healthy as possible and then the revenue to our courses + resume and mentor services tends to follow.

Have you pursued other online businesses?
Yes, several! I tried launching jdOasis.com back in 2011 but was never able to get the same traction that WSO enjoys. I think this was both a function of timing (2011 was much different vs 2006) = much more entrenched competition and me not doing a great job at building out a better launch plan and founding team.

I also started AmmoAudio.com with my cousin back in 2015. Once I saw one of his creations that he made out of his "shop" in his backyard in Georgia I convinced him to start selling them and I helped them get online and start promoting it across various publications. It did relatively well and quickly broke 6 figures but I think there was a limit to where he wanted to take it, so I decided to stop in early 2017 and just grant my equity back to him and his partner.

At that point I still believed it could be a very successful business but the margins were tough and to scale it more would have required a lot more risk and investment. As of now, it's still humming along :-)

How many people have you been able to meet from the forums offline?

More than I can count...if I had to guess I'd say probably over 1,000? Back when we hosted the large WSO events in NYC that was 300 each time and we did that for 3 years in a row if I remember correctly :-)

Thanks for the questions!
Patrick

 
Apr 7, 2020 - 6:04pm

Thanks for getting this off the ground, Patrick. Excited to see the reaction from the community.

One follow-up question for you, as a comparison from then to now: How have your priorities changed? What was something that was really important to you in 2006 that you couldn’t care less about today, and vice versa?

Array
 
Apr 8, 2020 - 11:13am

How have your priorities changed? What was something that was really important to you in 2006 that you couldn't care less about today, and vice versa?

Thanks for the questions. On a personal level this is easy... in 2006, I was more focused on career, on the business and on chasing women. In 2020, I've definitely found more balance -- I still work hard but I like to think it's more efficient, I unplug more often, especially on the weekends and try to decompress with my family and trying to be a good dad. In 2006 I'd work ~60hrs per week in PE and then after hours and on the weekends I'd work on WSO ~10-20hrs/week and party at night with an occassional poker night thrown in :-).

I'd say another shift for WSO specifically has been with my team. Whereas before my focus was on finding a decent developer that could help us with all the site issues and not bankrupt us, now my focus is much more on the business and content side since we've grown enough to support more developers full time.

 
Apr 8, 2020 - 7:13am

Thanks Patrick! Looking forward to seeing how this evolves.

What are some things about being a father you wished somebody told you?

How have your views on money/wealth evolved from your IB days to now?

What keeps you up at night?

What do you want to be doing in 10 years? 20 years?

 
Apr 8, 2020 - 2:10pm

ha, these are tougher...but I'll try:

What are some things about being a father you wished somebody told you?

I actually expected it to be difficult and overall having 3 kids in 4 years is a bit insane, but I think it can also be a lot of fun with the right perspective. Everly (4) and Ronan (2) are just close enough that they've been playing together for ~8+hrs a day while stuck at home and that has helped (usually).

In terms of actual advice, I wish there was more out there surrounding parenting styles and research. Terry and I have adopted a strict but loving mentality with a strong bias toward emotion coaching...but this was all new stuff to me and I know it's super different from how we were raised...so sometimes there is some doubt if we are being too accomodative with emotions (it doesn't help that our 4yo girl is sharp as a whip and very strong willed).

For example, the research on praise and not creating praise junkies is really interesting...ie not saying "good job" but replacing that with "you did it" is subtle but I think an important distinction -- not chasing your kids and screaming "be careful" all of the time...if it won't kill them or break an arm, let them learn by falling and trust that they know their limits. Some very counterintuitive modifications we've made like that would have been helpful to think about BEFORE we were in the middle of the chaos :-)

How have your views on money/wealth evolved from your IB days to now?
Largely unchanged. I was lucky enough to be taught about the stock market and investing from a pretty young age (my dad as a doc always invested) and that has served me well.

I think I still live below our means but I do spend on experiences (nice dinners, vacations, etc)... expenses are WAAAAAAY way higher than they were even 5 years ago with the kids, but with Terry still working part time we're doing ok and still saving/investing for the long term + education.

I still view money/wealth as just a tool to live the way you want and to have freedom...also just a way to keep score for WSO and ensure we are growing/healthy. I have conflicting thoughts about how much $ I'd like to pass onto my kids. I think enough to allow them a comfortable life but I don't want them to know that in case it is demotivating...I think that can do a lot more mental harm than good.

What keeps you up at night?
Very little to be honest. The stress I experience now is usually mild and I'm usually so exhausted that I just crash by 11pm. I think life is too short to lose sleep and as any of my old friends would tell you, I am a notoriously good sleeper (like 15+hrs in high school easily if allowed). If WSO fails or eventually becomes irrelevant would it hurt? hell yes. would I be destroyed from it and not be able to find interesting work after? hell no. so why worry? just do the best you can each and every day and make sure your heart is in the right place and deal with the outcome with the right perspective :-)

What do you want to be doing in 10 years? 20 years?

Ideally traveling a lot more since my kids will be older and it won't be such a nightmare. Careerwise I could very well see me still be running WSO full time with plenty of other side projects. In 20 years, I'm guessing I would have transitioned out of the CEO role and handed the reins to a younder pro with a lot more energy.

In terms of selling the business, I think it's much more valuable to me as a lifestyle business than it would be to investors. Now that could change in the next ~5 yrs as we are getting more intentional about driving top line growth (rather than pouring every cent back into community), but I suspect that any offer I receive will not be enough to make me step away since WSO the community (and business) is like my 4th baby :-)

I hope that answered your questions...happy to expand on any of them.
Patrick

 
Apr 8, 2020 - 2:39pm

Interesting response about parenting styles. I suppose I never gave it much thought since I don't have kids, but perhaps now is the time to think about it in preparation.

Do you have any good articles or books that lay out the approaches or why you prefer the approach you and your wife adopted? Not being over the top in praise or being a helicopter parent are certainly goals of mine in the future.

Commercial Real Estate Developer
 
Apr 12, 2020 - 11:18pm

WallStreetOasis.com]<br /> ha, these are tougher...but I'll try:</p> <p>[quote:
not chasing your kids and screaming "be careful" all of the time...if it won't kill them or break an arm, let them learn by falling and trust that they know their limits.

Good stuff, this by far has been my biggest difficulty because it gives me anxiety. I know there are some/certain things that we can control and anticipate, so I've always tried to control and mitigate those in order to protect my kids.

I'm trying to get better at it and I think the more you have, the easier it becomes to just "let go" a bit.

 
Apr 8, 2020 - 7:48am

Count me in the ranks of prior users who stumbled back in during quarantine. Very glad to see life treating you well Patrick. This site definitely helped me break into finance 8+ years ago (from a non-target!), glad to see it's still alive and kicking.

“Millionaires don't use astrology, billionaires do”
 
Apr 8, 2020 - 9:04am

Nouveau Richie Great to see you back man. Gotta thank CompBanker for putting getting the ball rolling with his post over the last two weeks or so. It really brought a lot of folks out of the woodwork for this.

Patrick, thanks for getting the ball rolling with this. It only makes sense that you're the first to do this then and now post.

Just looking at things, especially from when WSO first started as iBankingOasis and how it's turned into something so huge, I honestly think that WSO has given you a strange vantage point, as an outsider looking in. I don’t think much really changes. Considering how long WSO has been around, what are the biggest changes you’ve seen and where do you think things are headed? In light of the whole Coronavirus issue, do see it accellerating anything?

It’s crazy to think that WSO has been around for as long as it has and continued to grow, year over year. What advice do you have for folks who are interested in entrepreneurship and starting their own business? It can be anything from idea formation to scaling to managing the technical side of things to who to partner with.

One thing I’ve always wondered is what drove you to start WSO?
Having been to a few of the meetups, do you have any favorite stories from meeting WSO members?

 
Apr 8, 2020 - 5:55pm

Considering how long WSO has been around, what are the biggest changes you've seen and where do you think things are headed? In light of the whole Coronavirus issue, do see it accellerating anything?

The biggest challenges definitely in being a forum based site that grew up on organic search traffic based largely on the volume of it's UGC but as Google shifted from a URL based ranking system to a more brand/full domain algo, the low quality threads and technical SEO matter much more to our growth (it stopped going up automatically near the end of 2012).

Organic traffic has been a struggle for the last ~8yrs that we wrestle with with some years up, other years down, but we are also diversifying away from Google aggressively and driving now over 600,000 engagements across our social channels each month and our mobile app keeps picking up steam...so I'm still confident we can make this pivot successfully with our strong brand and reputation. We also have a lot in the works that will be announced in a few months :-)

In terms of Coronavirus, the last few weeks has been super odd. When the world was melting, markets crashing and everyone was panicking in mid March, we saw a rapid drop in traffic, but that has recovered and the activity on the site is now at an all time high in terms of active users (ie meaning not lurkers/visitors, but actual commenting/posting)...I do see this accelerating the sales of our online courses and we're seeing some of that as students are stuck learning from home and many won't be able to do their summer internships as planned, but I think it's a bit too early to predict what lasting impact it will have.

One thing I've always wondered is what drove you to start WSO?

Part fear of losing my job again (was fired from my first gig in PE unexpectedly), partly because I was working ~60hr weeks instead of 90hr weeks (tons of free time when single!) and read Forbes 30 under 30 article and it struck me how straight forward the businesses were. Also, I figured it would be fun and we could add a lot of value.

Thanks for the questions and welcome back to you!
Patrick

 
Apr 8, 2020 - 10:05am

He is back. He posted some racism against a black poster a week or two ago that had to be deleted and now goes by "Winnie the Flu"

Commercial Real Estate Developer
 
Apr 8, 2020 - 10:04am

Morning, Patrick. Great idea.

A couple questions:

  • How have you successfully monetized the site to the point of making a living from it?

  • I know there is a podcast and the various services WSO provides like resume review. Are there plans to expand into other media platforms such as YouTube?

  • In terms of your career and your business, what gets you excited? What makes you get out of bed in the morning?

  • In your opinion, what are your top 3 all-time greatest threads or posts made on WSO?

  • Who is your least favorite verified poster? ;)

Commercial Real Estate Developer
 
Apr 8, 2020 - 6:17pm

hey CRE, thanks for the questions!

How have you successfully monetized the site to the point of making a living from it?
Well the first 5 years I really couldnt but then with the release of the courses and services and in the early days the vertical ad network, we were able to get to a few hundred k in revenue which was enough to support myself and a developer.

Eventually we were doing well enough that we could get rid of all 3rd party ads and just focus on the best UI/UX possible (of which we fail sometimes but we're trying)...

I know there is a podcast and the various services WSO provides like resume review. Are there plans to expand into other media platforms such as YouTube?

We have a Youtube Channel https://www.youtube.com/channel/UCxILKCPvwWBYauA8N3ri8Sg?view_as=subscr… but it's admittedly not built out very well. We're trying to get better at taking the pod content, monkey to millions, moving up, highlights/snippets + other content and build out an audience there but it's tough when we also have LI/FB/IG, etc to monitor that get 100x the reach already compared to our efforts there. We still need to get better!

In terms of your career and your business, what gets you excited? What makes you get out of bed in the morning?

I think WSO still has a lot of untapped potential. We have an incredibly strong brand an amazing community and a wealth of wisdom. I get excited when I get emails from members thanking us for creating the platform and when I hear everyones success stories :-)

In your opinion, what are your top 3 all-time greatest threads or posts made on WSO?
Hard to pick just 3, but these are gold:
https://www.wallstreetoasis.com/forums/immigrant-homeless-broke-af-but-…
https://www.wallstreetoasis.com/forums/my-private-equity-recruiting-pro…
https://www.wallstreetoasis.com/forums/you-are-a-bottom-bucket-analyst-…
Who is your least favorite verified poster? ;)
plead the 5th here :-)

 
  • Analyst 1 in IB - Ind
Apr 8, 2020 - 10:46am

You know those youtube comments under some old rock song where people are like "I'm nostalgic for that feeling that I've never experienced!"?

same goes for Mis Ind. how I wish I was around back then! Seriously can't believe it's soon to have been some fifteen years and that I was running around catching butterflies back then...

Speaking of old users, any interesting and shareable insights looking into how long users stay active on the forums over the years and things like quality/frequency of posts over time? Would be interesting to see how prospective monkeys engage/don't engage with the forums as their careers progress and things like that.

P.S. Should totally publish a little book with golden bananas on it with some of the greatest wso stories/posts. Or maybe an official history. Or maybe a market/political commentary as reflected by what wso kids are posting about. Wouldn't that make a fun gift for some of the old-time posters?

 
Apr 9, 2020 - 7:35pm

ah yes, good ol' Mis Ind ! and bankerella - some classic posts from them.

Speaking of old users, any interesting and shareable insights looking into how long users stay active on the forums over the years and things like quality/frequency of posts over time? Would be interesting to see how prospective monkeys engage/don't engage with the forums as their careers progress and things like that.
Back when I was at Wharton in 2008-10 we did some cohort analysis like this...I think it would be fascinating, but we just don't have the data analytics capability (or budget) yet to really dig in here.

We've gotten better with the use of Tableau and taking a lot of our site data to get better insights on what is going on daily (like active users, total posts, comments, SB/MS and overall community health), but admittedly cohort data would be cool. Either like quarterly cohorts back to 2006 and then those split into prospective vs more senior pros... we'll get there :-)

Speaking of old users, any interesting and shareable insights looking into how long users stay active on the forums over the years and things like quality/frequency of posts over time? Would be interesting to see how prospective monkeys engage/don't engage with the forums as their careers progress and things like that.
yes, this would be awesome. The only time we broke the bank to do something like this was when we sent out like 100 silver banana deal toys to the members who had reached King Kong status. I think we may be close to do another batch soon.

 
Apr 9, 2020 - 11:40pm

Oh damn, Mis Ind - that’s a real blast from the past! I was around for the IBOasis days, trying to figure my way into finance. She helped fill a much needed void in providing the female perspective from within the industry. It’s a shame we don’t seem to have more female posters.

The world has changed, and younger women entering finance now have more support in the way of mentors and reference... And IB now is, relative to when I was in it, a “kinder” place to be (for everyone). But from a career progression standpoint, I think women at the VP/ED/Principal levels (sell side and buy side) would benefit from more guidance and transparency on how to make it to the MD/partner ranks.

@WallStreetOasis.com" - I’d love to see more of that (guidance for mid-level professionals wanting to make MD/Partner) - for women, or frankly for anyone in general. That’s something I’m personally trying to navigate. It’s one of the reasons I’ve been less engaged with WSO - I’ve found fewer relevant topics for my own growth. WSO tends to trend younger - helping people get their foot in the door, and maybe up to that middle rank. But there’s less on how to navigate to the top. That, and moving into VC has occupied a lot of my personal time in building a network, and separately providing mentorship in real life, has been rewarding.

 
Apr 8, 2020 - 1:12pm

Thank you for everything and for building such an awesome site and community!

Honestly, I have never used this site for the benefit of my career. I always could navigate pretty well myself. However, it has been much much more useful than that.

When I was a young banking analyst and research associate, I thought that I was the only person getting brutalized by crazy associates and MDs. Turns out everyone experiences that! WSO has been a great site to blow off some steam and relate with the other monkeys in your same shoes. From a mental health perspective, that has been far far more valuable than any recruiting advice out there.

 
Apr 8, 2020 - 3:14pm

From a strategy perspective, was it a purposeful decision not to replace featured content creators like Eddie Braverman or were you just unable to find someone to fill his shoes? As an older user, I always found his content to be a good reason to "come back" vs. a lot of the repetitive user-driven content.

when you're accustomed to privilege, equality feels like oppression
 
Apr 9, 2020 - 7:54pm

Not strategic at all...I actually tried several times to get Bess Levin who used to write for Dealbreaker as well as Amit (former Leveraged Sellout blogger) to start writing for WSO, but was never successful.

It's more just been an acknowledgement that we haven't ventured into paid bloggers because no matter how good they are, they can rarely move the needle enough to warrant the spend. Eddie was a special breed and a perfect match for WSO. He was admirably consistent for many years and he was kind enough to share his wisdom and not bankrupt us while we were still in our early growth stage.

Since so much of our traffic is through long tail organic search it's still very hard to justify paying for content unless it's directly leading to a conversion (I think this is why you're seeing so many news organizations having to slash staff as everything moves online). In other words, even Eddie's most popular posts would only be like a tiny fraction of the traffic to the site in a given week... outside the top ~50 pages on the site, each one is ~0.1% of site traffic or less...say an amazing writer could somehow post something that gets on avg 10,000 pageviews...if you do the economics on an eCPM basis, unless we were running obnoxious pop-up and interstitial ads like Forbes.com, you're basically only making ~10-30% back on what the article costs.

The $ per pageview if you're trying to survive off of ads is just brutal. The economics of forums is not much better since most people want to read the content and interrupting them is usually in direct conflict to a good UX.

As more of our reach has shifted to social over the past year, you could make and argument that we could find a way to make it positive ROI, but it would really need to be a mix of educational/course content in order to drive revenue.

Not sure of the rambling above makes sense :-)

 
Apr 8, 2020 - 5:15pm

I'll play on a more limited basis.

When did you first join WSO?
Not sure when I started reading it, but it was before I left NYC in July 2007. I started my account sometime that fall/winter as an associate at a (tech) boutique IB after doing 2 years in ops and then trading at GS and then started back over to do 3 years in IB at Citi.

Why did you join?
I wanted to maintain a connection to what was going on in NY after moving to a smaller market after I left Citi.

Is there anything else you'd like to share?

Read my post history...have shared it all before! I keep coming back because I left banking in 2012 to start a company, and like when I left NY and joined WSO, I still like to hear about what's going on. I mostly just click through stuff on conference calls that I'm not leading.

 
Apr 8, 2020 - 6:09pm

Great to see you back. You should do your own thread over the weekend or something if you have more free time then. Your perspective has always been valuable, you're grounded and thoughtful in a way fewer people here are.

I would get a lot of value out of seeing you engage with some people's questions.

I am permanently behind on PMs, it's not personal.

 
Apr 8, 2020 - 7:34pm

Patrick, when I had my own professional challenges WSO helped me find the path I needed to build a career, what would have been your plan if WSO failed to take off? How do you think the career you have built for yourself and the path you have taken might ended up differently? Lastly, when you were getting this community off the ground, what were the largest risks you needed to take?

 
Apr 9, 2020 - 8:10pm

what would have been your plan if WSO failed to take off?

Depends on what stage you are talking about...if you mean early on, I probably would have started something else and just kept trying. I got lucky that try #1 was successful (as I mentioned above, several other attempts have not been).

I think coming out of Wharton if we didn't figure out how to generate enough revenue to support me, I would have had to scramble and I would have likely tried to get back into private equity or any other type of investing role. I really liked PE and getting to meet successful CEOs/CFOs.

How do you think the career you have built for yourself and the path you have taken might ended up differently?

Tough to know for sure in hindsight but I think I probably would have tried starting at least a few more businesses. Probably something in retail with a technology bent.

Lastly, when you were getting this community off the ground, what were the largest risks you needed to take?
very, very little. I started it while working full time in private equity and had to invest very little capital since my co-founder set up version 1.0...so we spent maybe a total of like $2k in year one...then as it scaled, I bought out my co-founder for $15,000 when it was still under like 1,000 members since he was too busy getting his phD at MIT to work on it as aggressively as I wanted to.

So from 2006 - 2008 it grew steadily while I worked on it part time...still by 2008 was bringing in I think under $60k/yr which I was dumping back into the site. then I guess you could say I risked $15,000 and after that the next big "risk" was me not recruiting in 2008 once I was at Wharton for a summer internship. Instead I applied to a bunch of venture programs and even got a few small grants to support us over the summer.

Basically, I had 4 years of "incubation" before it had to be a "real business" which I think was one of the reasons it ultimately did so well. There were no investors, no debt, I was committed to it and we never let costs get too high.

So I would say it's about as conservative a start as you can get and not something admirable where I took some sort of leap :-) -

I actually think this is a huge misconception a lot of young potential entrepreneurs are fed... stuff like "quit your job! take a risk! you only live once!" ok yeah, sure, say the 100+ entrepreneurs that made it...but what about the other 1,000+? Yes, you need to take risks to succeed but they should be calculated risks.

If you can build up your side hustle to ~50% of your salary and you are smart with your $, then I think that is a great time to leap...but doing it before I think is a bit reckless in most cases.

 
Apr 9, 2020 - 10:15pm

Hey Patrick,

Like some others, I've drifted off over the years as life has changed but just wanted to drop in to say hi as well, and to wish you well!! You've built something truly special that has lasted longer than most companies.

Alex

Alex Chu www.mbaapply.com
 
Apr 10, 2020 - 6:38pm

Thanks for doing this Patrick. The community has been an invaluable resource to me over the years and the fact that your dedication has not waned is inspirational.

My questions:

  1. Could you expand more on your experience living in Buenos Aires? When did you decide to do this? What made you decide to do this? Was this right after business school?

  2. Was it a difficult adjustment at first? How did you pick Argentina? If you could go back in time, would you do it again? What were the pros and cons?

The fool thinks himself to be a wise man, while the wise man thinks himself to be a fool.
 
Apr 13, 2020 - 2:49pm

Could you expand more on your experience living in Buenos Aires? When did you decide to do this? What made you decide to do this? Was this right after business school?

Living in Buenos Aires was more about taking control of my life rather than going back into corporate America. As part of going full time on WSO, I figured it would also be a blast to be somewhere I wouldnt have been able to be otherwise and travel a bit, get my Spanish back (my mother was born in Cali Colombia and I had gotten very rusty, even with all the schooling) and just explore the world.

I probably decided on Buenos Aires after my first year at business school once it seemed running WSO full-time wasn't just a dream but an actual reality that was open to me as revenue scaled. It was still a bit scary but the excitement of it far outweighed the downside in my opinion :-)

BA just seemed very friendly to Expats and a great hub to be able to explore more of South America... so, that was that!

Was it a difficult adjustment at first? How did you pick Argentina? If you could go back in time, would you do it again? What were the pros and cons?
Yes, it was a bit tough at first but what made is MUCH easier is I found a roommate (from UNC) that had been furloughed from his Big Law job, so he was down there just traveling/partying with his year off and enjoying life as well. I think while that helped make friends, it probably hurt my spanish development...that was much harder than anticipated, even with my spanish background given how different the spanish is there.

Yes, I'd go back and do it again in heartbeat but it wasn't easy or all fun.

PROS: pushing comfort zone, seeing new areas/cultures, being free to do whatever I wanted any day of the week (I see these as major Pros and the cons listed below are more minor)

CONS: it took me a while to make some good friends and it often felt temporary since a lot of expats would come and go. then with friends that I made that were from Argentina it was tough to ever feel truly integrated since you are kind of seen as an outsider (naturally) -- even though I met some incredible guys that even invited me to their small home town in Santa Rosa (like farmland in Argentina). Feeling a bit disconnected from friends and family back home...even with Skype calls, etc it was tough to stay super connected.

I'd say probably the biggest con from my time there wasn't the city or the country but the fact that I started dating a woman there about ~5 months in that ended up having a lot of mental health issues. It was a tough relationship (a bit of an understatement) and one that I ended once I left BA, but I feel like it was very draining and I often look back and wonder why I didn't get out earlier. in hindsight, it was a mistake but tough when you are "in it" to see clearly!

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