Posts tagged San Francisco
Serial Investor 9/5, savage rapper on the weekends: interview with Alejandro Rioja

Today I am interviewing Alejandro Rioja.

He is an entrepreneur and investor who moved from Bolivia to the States.

At only 23 years old, he just made the cover of Forbes & I'm excited to share some of his best business tips and vision of success.

We’re also going to talk about his alter ego, Young Slacker who is the complete contrast of his geeky side in real life, because he’s also a latino rapper who sings about girls, drugs, party and so on.

He inspires through his ability to embrace the different facets that make him truly unique and unapologetically HIMSELF.

He's also highly ambitious and constantly crushes business and personal goals despite starting from zero, letting his passions lead him.

It's not About Virtual Reality, it's About Recreating the Real World
Estimated reading time: 7'

Estimated reading time: 7'

I met Isaac at a house-party at my place last year.

We did not have the most usual conversation on a Saturday night as he was telling me how unhappy he felt at work, and that he was considering quitting and going on a trip.

I encouraged him, as I always do with people who want to follow their heart, but you how it is, a lots of people dream of doing that and never actually take the step.

Isaac wasn't one of those.

The second time we caught up, he had quit the same day and was leaving the following week to Europe and Asia, on a one-way ticket. He was literally shrieking and jumping up and down, of excitement. Obviously, champagne was on me!

The third time we met up, he had just gotten back from his trip and was visiting LA, so he had to tell me the whole story over lunch.


“I’ve been passionate about programming for as long as I can remember.

At 13, I became obsessed with Scratch*. I really loved that you could make shit out of nothing, I was like that’s awesome, I can build my own world!

After 3 months, I built up a word-search game that got featured on the front-page of a website.

I wanted to do more of that, but back then in 2010-11, I didn’t know it was possible to do this for a living, I wanted to build websites and apps were not really a thing yet.

My parents didn’t know any of this shit so they couldn’t help me, they were like follow your passion but to an extent, and live a normal life after that aha.

A couple years later, I investigated and found a programming summer-college at Harvard that taught me a little more, though was very isolating because we were basically running a computer inside a computer, which took a lot of memory and slowed down the whole thing, preventing us from being able to actually build stuff.

Fast-forward to my first programming meetup in NYC. I dropped a note on the group and asked if somebody wanted to go with me since I was a high-school kid and didn’t know anyone.

A girl responded and we hung out over pizza. She did not go to college, so I was like “Wow is this something you can do?” It blew my mind. At the time, I was going to private school in NYC and everybody hated school, period.

A few months later, I participated in a coding boot camp over the summer. It cost a fortune and my parents didn’t want to pay…


“What do I do now?” moment nr 1:

I contacted the founder and asked if I could do an internship there. I kept emailing him till he finally said yes. Hustling my way in!

I love that when this guy wants something, he makes it happen and takes chances.

This internship was life-changing because it was still school, but everyone was coming from all these different backgrounds and actually wanted to be there and learn. These were real people, older, not just high-school shitheads… One guy was in the army, another one was a baseball player, one was a surgeon, etc.

We had this thing called “Feeling Friday”, where everyone would stand up and share their feeling of the week, and one time I started sobbing and say, “this is my home”.

When the summer ended, I had to go back to high-school for a final year. It was brutal. I had had a flash of how my life could be over the summer and it certainly wasn’t school.

I got in trouble all the time because at this point I couldn't care less. The principal thought I was crazy so I got hooked up with the school psychologist, and I was able to skip the worse classes I had to chill with her and chat about our common hatred of the place.

Eventually, I managed to get an internship to skip all the other classes I hated.”

This is what happens when the educational system insists on putting people in boxes rather than trying to understand why they misbehave…

“At that point, I had to apply to college as my parents were pressuring me so I did this for a year, but I was dreaming of San-Francisco, the geek heaven.

I asked the founder of Flatiron for contacts and he helped me get an internship in SF. My plan was that they’d love me so much they’d hire me, but of course, none of that happened. They were giving me no responsibilities whatsoever and at the end of the internship I had no plan B, but I still had a place so I decided I’d just figure things out and it would work out.

I spent a year doing freelancing, being a Postmate-career, using my savings, but at some point, it just wasn’t going to pay my rent".

I could totally relate to this…When you sign up for a place on a long-term, it says a lot about your intentions and commitment, and it gives you a push to make things happen.


“What do I do now?” moment nr 2:

"I did a lot of networking, went to hackathons and ended up being approached by this guy who was looking for an engineer to launch his start-up. That was a month before I’d have to go back to college for want of anything better.

His app was pretty cool so we decided to give it a shot. We moved to the Tenderloin (NB: the worse neighborhood of San Francisco, frequented by drug dealers, criminals, and prostitutes).

After we got fundraising, I became a co-founder, we used the money to get a better lifestyle, we hired people, tried to make it work but it just wasn’t going anywhere.

I was in a social cage, it was a mindset thing, all I could think about. As things were going downhill, I met this cute girl, and we literally lived together for an entire month. I was craving social interaction at that stage. On a Friday, she came home (which also was out office) early and we started to hang out. My co-founder freaked out as he saw that I was phasing out, asked me “do you really want to do this, you’re not focused?!”, and he let me go the next day."

It happens SO often that when you don’t want something, you fail it on purpose so that somebody else takes the decision to end the situation, and sets you free.


“What do I do now?” moment nr 3:

"I left and chilled on my friend’s boat in Sausalito. It sounded like a dream but it was pouring every day and there were no bathrooms…

So I got a job in a startup.

My boss was difficult and I could not deal with it anymore – to be honest, when I quit, I first one to leave but since then almost all my coworkers walked the walk.

I was planning on traveling to Europe and South-Asia with a friend but on the first night, she got a call from her boss and had to go back home right away. She ditched me.


“What do I do now?” moment nr 4:

Isn’t it interesting to notice that every time you face an obstacle, and things don’t go the way you planned, this actually gives you a chance to level up?

Well, I had no return flight and had gotten rid of my apartment in San Francisco so there was no way I’d turn back. It was slightly exciting and slightly terrifying.

I went to 9 countries in 5 months (Prague, Spain, Italy, Germany, France, Switzerland, Thailand, Vietnam, Japan…), did some freelance, traveled and taught kids some English. Even though I originally wasn’t planning on coming back, it felt very temporary because the language barrier made it difficult to have meaningful conversations. So I came back.

Now, I’m switching my career to Californian politics, housing, local stuff. It is more meaningful. I’ve had to live in unsafe and uncomfortable places and areas during my life, and I want to make a difference for others. 

Also, housing really is a centerpiece of understanding America’s decay. Once you understand that America’s problems are totally made up and we’ve brought this on ourselves, you find ways to fix it.

We don’t have to be in a shit show.

Our environment doesn’t have to literally burn in front of us. We just need the courage to say that we failed and it’s time to try something new.

In fact, I’m not really switching from programming at all. I see these things as tools — as means to an end. It just happens that programming and creating apps are a great way to reach people.

Before having to face all those "What do I do now moments", I think I was afraid of what was going on around me. You look around and it’s hard not to be scared. But that’s how they get you. That’s the only way Trump will win, is if we become scared and desperate. I’m not afraid anymore because we’re screwed by our inaction. 2017 was a year of roller-coasters, 2018 is a time to act. Go do whatever you need to do!


(*colored blocks that you drag & drop like puzzle pieces instead of typing codes)

Would you rather build your own virtual reality or recreating things on the real world?
— Isaac Rosenberg
Curiosity Doesn't Kill the Cat
Estimated reading time: 6'

Estimated reading time: 6'

I met Ruhana at a concert organized by common friends.

One of the biggest secrets she rarely discloses to anyone is her age. And when we became close enough, she told me she was 18. You could not tell by the way she speaks.

She can talk about any topic for hours.

She has this talent for connecting with people and connecting people: you put her alone in a room and she will leave with five friends.

She studies, has two jobs and multiple side-projects, and is part of various ethnic, feminist, spiritual and artistic communities.

As we were chatting about her involvement with minorities, I asked her where it all started.

"Far back. I come from a highly disciplined and traditional family in New Jersey. I studied at a preppy private school. Money was never an issue. People's family name and size house represented their status. One of my friends owned a jet, another one had a monthly $500 allowance; that was normal. Naturally, my friends and I selected people to hang out with based on level of intellect and status. Kids from public school were considered 'improper and unsheltered'. We also would select friends according to their ethnicity. There was only one African American in my school and no Hispanic students. Even as a first generation Bengali American, possessing fair skin was the standard. I always made sure to hide my darker hands under the table, or in my pockets. 

One of the core values that was instilled in me since attending that school was practicing discipline to earn respect.

At home, my parents were expecting me to know everything about all sorts of topics (physics, politics, conspiracy, etc) from a very young age. And at school, I'd get a fine if I wore grey socks instead of white, for instance. We were all expected to go to Ivy leagues and land a 6-figure salary job. The GPA determined my entire life and my worth to society. The "A" defined confidence, and I would beat myself up for anything less than that".

I tease her about her current 4.7 grade on Uber.

"Yeah I don’t understand why Uber drivers are judging me so hard...!" We laugh.

"On the other hand, everything was granted, including the teacher's behaviour. Students would have their parents make appointments with the principle if they were unsatisfied with their fixed grades. To be honest, I never realized I was entitled to good treatment until I went out of that situation. I never even learned how to register for my own classes or find classrooms on my own since we were given designated point of contacts to find classes for us on the first day of school. 

When I turned 13 years old, I went on a trip to a spiritual Islamic retreat in Tarim, Yemen, for 40 days. In that specific city, it is said that the sun purifies the dirt of your soul.

We spent the days praying in a sacred atmosphere, which opened up the doors to a spirituality that I had never been exposed to before. I understood that life was more than the materialistic things I was exposed to back home. Through a new perspective of religion, I discovered a deeper relationship with a higher being, and gained a new outlook on life and people.

Each Friday evening, a spiritual celebration was taking place where a congregation of women would be gathering, singing, dancing and playing instruments. Each person would play their own music, though somehow manage to all sync together. They were all living fully in the present, enjoying with what little they had. Their inner beauty and independence was glowing.

There were people from all parts of the world; Germany, France, Russia, Malaysia and so on. They had different ideologies, different upbringings. I figured that everybody's life is customized to bring up the best of themselves.

What happens in their lives defines their personality and crafts their motives for doing things.

 Once, a clerk at a store, a complete stranger, invited my family and I over for dinner during the stay. She hosted us in such a grand manner with a huge feast of kafsa, an enticing Arabian dish of perfectly seasoned meat and rice. The rest of her family members sat down to put henna on our hands. It seemed so unreal I got skeptical. I supposed she would be asking us for help after she hosted us. It was hard to fathom that she hosted us purely out of kindness. I asked her why she was feeding us in Arabic. And she responded with one word as if the answer was obvious, “Ya’ani adaab.” “I’s etiquette.” A sense of morality came to thin air and I wondered, “Why aren’t we this nice in America?”.

Again, this made me embrace and respect each individualities more, differences and viewpoints, as well as taking pride in my own views and values and learned to differentiate between the real and the fake. I became interested in understanding behaviours and people.

I redefined knowledge: I was not learning for the sake of learning anymore, because of peer pressure or for the best GPA, rather, I wanted to learn out of genuine curiosity. 

Obtaining supplementary knowledge rather than studying the American education system's redundant core curriculum seemed more important to me. So I decided to homeschool for the next 5 months upon my move to California at 15, unaware of the detrimental social consequences. Although the silently killing isolation drove me insane, I was able to learn more about myself and internalize everything around me.

In California, the state of liberalism to the max, I referred to myself as a FOE, fresh off the East. We’re pretty ignorant about racial diversity there. I re-evaluated how I saw people of color; taught myself how to humanize people based on John Locke’s principles of natural rights. I unlearned racist behavior and mentality.

After I switched over to public school, I also began to understand the importance of sisterhood, tied with female empowerment. Insecure but “popular” girls at Santa Clara High swooned over immature foolish boys. Subtle sexism was everywhere from high school to corporate employment.

From body gestures to language, gender discrimination became more prevalent as I started college. I decided to experiment with men; 21 men in the span of three months to be exact. I kept a mental report of my dates' different characteristics associated with races, occupations, ethnicity, their views of women and expectations. Getting hugged rather than having my hand shook in a group full of men; being called an attention seeker for dressing too “provocatively”; being asked why I come home late on the weekends; encountering mansplaining on a daily basis by bosses, colleagues, and friends; my 40 year old male roommate denying that sexual assault is even a real thing; being asked why I go to the gym because my figure didn’t imply it was necessary; friends not believing things happening to me non-consensually. Getting mistreated as a women subtly was something I could no longer tolerate. The values of self respect I learned at school were put in place in my childhood for this reason. Self respect implies the intolerance of bullshit. And in hopes of ending such patriarchal bullshit, I’m planning to start a nonprofit to empower young women in a few years down the line. I embrace my own self. I know who I am, what I like and what I want.”

By switching her focus from "having the best grades" to "real-life experience" through being confronted to different social, spiritual, artistic and ethnic environments, she has become exponentially more curious, open-minded and comfortable networking, and so can anybody,


Quality Over Quantity
Estimated reading time: 3'30

Estimated reading time: 3'30

I've always admired Minimalists. Those people who flip the bird to our materialistic society and are satisfied with the bare minimum.

So I was curious to know how my roommate Mark had become one.

"It was back in 2010. I was a typical Investment Banker in NYC at the time. Roughless, ultra ambitious, liberate materialistic. In the world I lived in, the very rich wanted to be ultra rich and show that they had the good life. Money had become an ego thing.

To feel very happy for the rest of their lives, they felt that they had to be known, rich and powerful. Their lives were all about status, wanting more. First having a house in the Hampton, then in Saint Tropez, then becoming a millionaire, a billionaire etc. And I was on the fast track to becoming one of them.

My Managing Director at the time was deep into that lifestyle. He was spending 250 000 dollars a month on rent for different apartments. He used to eat brunch at Saint Ambrose, the kind of places that would gather the creme of the Upper East Side, where the table where you sit matters and displays your social status. He was also fascinated by models, young blonde Russians bimbos, which would eventually cause the end of his marriage.

One night, while I was celebrating Christmas Eve with my family, he asked to come over to his place. He asked me to stop by and have dinner with him because he had no one around him (his wife had left him and his daughter hated him), so I showed up. He cried.

That night, he said 'you remind me of myself when I was young'. At the time, I took it as a compliment, but looking back at it, I'd do anything to not end up like him. He was not happy."

"Two months after that night, the seed had sprouted in my head. I completely changed my lifestyle.

I quit my job, moved out of NYC, applied for Business school, somehow got accepted. I also got involved in a serious relationship, which was easier now that I had a 9 to 5 schedule and was free on the weekends.

Eventually, I decided to travel and had to get rid of all of the stuff that I could not carry around in a bag: I left them in a storage room and ended up forgetting about them.

When I got back home a year later, my things had been auctioned. Surprisingly, I was not upset, I actually felt relieved. I got forced to become a minimalist, but then I liked it. 

Here is how it works:

I only buy what I really need. I do not feel the urge to spend money on things anymore as much, and I'd rather buy one expensive thing than 10 cheap crap. 

For example for clothes, there's an app that I use called Stitch fix. They follow me on Pinterest, analyse my style and send me minimalist clothes, and I send back what I do not like.

2. I'd rather spend money on experiences anyways: travels, festivals, drinks with good friends etc... I'm a lot more content this way. 

3. Same goes with people, I'd rather have 5 reliable friends than 100 fake ones.

4. I have not become a hippy that does not care about money, but I do not rely on external factors (wether it is money, things, love in fact) to make me happy, it comes from inside.

5. I know that I have to take care of myself (watch my sleep, diet, health in general), be self-aware, know myself really well to make decisions that truly make me happy.  One tip to get to know yourself better is to start figuring out why you get angry: dig deep on the source of your anger (it could go as far as childhood). Once you understand yourself better, you also understand others and develop empathy. And as a result, you'll get less annoyed by others, happier.

6. I still want to be successful, but not to prove anything to other people. I do not care about other people's opinions anymore. I ignore their power games, the gossips, the politics. It is like poison.

7. Now I create value (I am a Product Manager), and it feels more fulfilling because I have a meaning.

Having money and being happy is not contradictory, as long as you have a purpose, I think.

Look at Warren Buffet. He is a minimalist, he is the ultimate role model, the second richest man in the planet, he lives a very simple life and he is happy."

One week later, as I was about to move to a different city, I got rid of 75% of my things so that everything could fit into one luggage. 

A first step towards the Minimalist lifestyle.

Anybody else has given Minimalism a try?
Invest In Yourself
Estimated reading time: 4'

Estimated reading time: 4'

The night I met my new roommate, I had just lost my job and was overly anxious.

After exchanging a few introductions, he told me that he had a lot of energy and could share some with me, preparing a “ball of energy” between his hands — if you can picture that. He approached me and asked to put his hand on my chest. Caught unaware, I accepted. 

After 3 or 4 deep breaths though, and without completely understanding how, I suddenly felt much better, like relieved of a weight...

Intrigued, I asked him if this “energy thing” was magical.

"- I did not believe in this either at first!

- So how did you get introduced to it?

- A few years ago, I started a pursuit of enlightment. I wasn’t a cool kid growing up. I was shy, not good at dating or with friends. I thought I’d have to live with that, that this was engrained in me. Until I learnt that it was possible to master social dynamics, and alter my own energy and vibration. I have learnt certain tricks: eye contact, charisma, confidence, body energy… Those are skills that you can train, like leadership.

In 2014, I had a depression, I felt that I was trapped, hiding behind a mask so friend recommended that I'd go to a landmark farm. It is a transformational workshop consisting in deep psychological work, that helps people break out of their limited beliefs in a group.

This was succesful so I tried other things. I've learned about chakras, I've participated in "Interchange", a counseling program, and the "Authentic Man Program", which teaches you the masculine/feminine dynamics. I've been to naked camps, where everybody opens up and gives love to each other, freely, without the constraint of clothes. I also do daily meditation and yoga for body awareness and have a Tantra lifestyle, which helps being conscious of my energy and the ones of my partners.

There's also the orgasmic meditation. It is another group experience during which you meditate and stroke other people while focusing on body awareness, rather than seeing it as a sexual experience. I used to not be attuned to my "energy body" so this was a vulnerable experience that unlocked emotions the first time: I cried for the first time in 20 years. In other words, you can compare this experience to the healing of your inner child. It also improves your relationships to others. The male gives, and the female receives. Once you do this, you break a lot of fears when it comes to approaching women...

Another impactful experience I've had was with psychedelics: LSD, mushrooms, Ayahuasca. Ayahuasca is made from a vine in the Amazon forest — it's cooked and you drink its sludgy liquid, while a shaman calls in the spirit. You feel that "Loving Mother Earth Spirit" enters your body, to heal you psychologically, spiritually and emotionally. You start having visions and puke out energetic patterns. It shows you what you need to see, for example, the next steps you need to take for your company. That's why Ayahuasca is known as the "CEO drug".

I personally had visions of my dad, whom I hadn't seen in 3 years. I bought a plane ticket to meet him and resolve our issues and forgive him. He passed away the following week.

- How can this be explained?

- All those experiences are created by you, your brain in the end, but set up by those activities. You cannot "pretend". Especially the ahayuaska that really gives you very strong body reactions, it is difficult to imagine that it is only the brain making things up.

Also I've once been asked to hold a kryptonite, not knowing the effect it would have on my body. And suddenly I started to feel extremely warm and had to undress, to then learn that kryptonites are full of energy, which spreads into you as you touch them.

- So do you feel like you are done with all those experiences, or are you still in quest for spirituality?

- There are no limits to human capacities, I've grown faster than I ever had, I am on an accelerating ramp. There's always the next workshop to attend, the next article or book to read.

- What have you learned so far?

- That the number one priority as as human is spiritual awakening, not money. I used to be cheap — now I'd rather invest in myself and it is paying off, I am much happier, self confident and can have intimate connections and experiences. The Universe is not random, there is a master plan, and everything is happening FOR us not TO us, so we have to listen to the signs, listen to our bodies and be present, in order to achieve enlightment".

It's not your Fault
Estimated reading time: 3'

Estimated reading time: 3'

I was having my housewarming party when I met "Philip from the Philippines". We were having drinks, listening to loud music and discussing how he had ended up in California. He had come to America with his mom and sister when he was three years-old to grow up on the West Coast, but he was not aware of the reason for the move until recently.

One day, while he was at college doing his homework when he received a notification on Linkedin:

"- This strange man was saying that he had been looking for me forever and that he was my dad. At first, I was skeptical and thought it was a scam... So I tested him and asked for proofs. He suggested that I’d send him my email address so he’d tell me everything I needed to know. Still suspicious, I gave him my spam address. 

15 minutes later, I received his email, so curious, I opened it. In there, in poor English, he was telling stories about my childhood. I read on. It’s when I opened the attachments that my heart dropped: There were a birth certificate and pictures of me and my family… I recognized my mother and my grandmother.

It felt like a dream or a movie. I was thinking “This isn’t real". 

My parents had met young, at school, and they loved each other. My mum was 16 and she had started her own business, after having learned to design clothes for Louis Vuitton, and my dad was an engineer. When my mother got pregnant with me, they decided to start a new life in the States, to offer me a better future. The plan was for my mum to establish herself first, marry an American citizen, get a house, and my dad would join us after he would finish his studies".

His mother and the American citizen fell in love, so she cut all contacts with his dad, and changed her and Phil’s names. Later on, she would give birth to his sister.

"- My dad told me about my original name, Abdelkarim, a Middle-Eastern name. Now my nickname is Abe. When he told me about my mother’s name, originally Edna (now renamed Edesna), that’s when I began putting the pieces together. It was the name that my auntie used when she and my mum used to fight... 

Growing up, all my friends at school said that my sister and I looked nothing alike. My step-father was abusive to me, but not her. After they got divorced, only my sister got to spend the weekends at his house. I had lost a father figure. My older cousin was the one who taught me everything, from playing basketball to dating girls. I thought that my (step) dad hated me.

Now I know why: I reminded him of my mother’s past. Right now, I am saving to pay back my student loans, but soon, I’ll get a ticket to visit my real dad, who now lives in Germany.

- What’s your conclusion of all of this?

- Well, this was painful, but it was a big eye opener. I have become stronger, a better person, I stopped hanging out with the wrong people.

I stopped feeling guilty, not good enough. And I have forgiven. I tattooed a Phoenix on my arm, the Phoenix rising from the ashes, symbolizing second chances, and a dragon, symbol of strength and wisdom".