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“If You Lack a Skill, Teach It to Yourself” The 5 Lessons I Learned Being a 20-Something Founder

I had the pleasure of interviewing Monica Weintraub, founder and CEO of Down to Donate, a donation subscription platform where…


I had the pleasure of interviewing Monica Weintraub, founder and CEO of Down to Donate, a donation subscription platform where crowdfunding and subscription services collide with the nonprofit world. By 23 Monica had traveled across the world to live in China, launched her first startup, New Life ESL, and had become a published writer in both local and international media outlets. Today, Monica’s first startup is under acquisition, allowing her time to work on her second startup where her real passion lies; within the nonprofit space.


Jean: Thank you so much for doing this with us! What is your “backstory” of how you become a founder?

I’ve honestly always known I was un-hirable. While I have a strong work ethic, I just don’t enjoy working for other people. At 21, I let an excellent scholarship in the US go unused and decided that college wasn’t for me, which could easily have been a mistake in today’s job market, however, I like to think I’m not doing too bad. I say I’m un-hirable because I can’t imagine having a boss, let alone making money for somebody else’s for-profit business. I have always been a good employee, held on to jobs for at least a year, and respected authority, but mostly I just wanted to get to the top as fast as possible. I have a knack for making my visions come to life, whether it be a gift for a friend, a vacation, a business idea, or a blog. I like seeing what I dream about become tangible and accessible. I’ve had my ideas shot down and laughed at so many times that I almost embrace the notion of failure.

Jean: What do you think makes your company stand out? Can you share a story?

My new startup is a product of my own frustration. Frustration within the US government, frustration within the way nonprofits accept donations, and frustration when it comes to thoughts and prayers getting in the way of action and donations. The world doesn’t need another nonprofit — we just need to better support the ones in existence that know what they’re doing.

We pride ourselves in being slacktivists (slackers + activists). We know if we get more people to give a tiny bit of money every month, tremendous progress can be made. We know that people are looking for ways to give back, but they don’t know who to give to or what to give them. That’s where we come in. We’ve curated a catalog of 15 nonprofits that all kill at least two birds with one stone. Our goal is quite small: we just need 20,000 subscribers over the next three years for each of our 15 nonprofit partner organizations to each be getting $10,000 every month. That’s almost $2,000,000 a year in donations all by millennials donating the equivalent of a pint of craft beer. The nonprofits we partner with are fighting for human right, race equality, gun control, LGBTQ+ rights, environment welfare, mental health awareness, and so much more.

Jean: Are you working on any exciting projects now?

Because Down to Donate is unlaunched, all I do is spend my time developing the brand, the site, the content, the relationships, and everything that comes with starting a business. Essentially, all of the boring stuff. All the while, I am in the process of selling a business, which is basically another full-time job. Needless to say, I don’t get much sleep and am always stressed out — the not-so-glamorous side of being a founder we are not having a conversation about.

Jean: Do you have a favorite book that made a deep impact on your life? Can you share a story?

In 2011, just before I moved to China, I started following Nasty Gal’s, Sophia Amoruso. I was fascinated with her style, her copywriting, her age, and the way she broke the rules when it came to branding her business. I watched Nasty Gal like a hawk, not even ordering often from them, but just obsessing at how on point the brand was. When learning about the release of #GIRLBOSS in 2014, I immediately ordered a copy on iBooks, and read it cover to end in under 48 hours. It was precisely the book I was looking for after following the brand so carefully and was released as I was developing my first business. I understood authenticity was the name of the game, and that people wanted to see you as a founder represent your company in all aspects. They want to see your picture and your personality associated with what they could potentially become a customer/client to. It’s about staying true to yourself while building a brand that people can resonate with. You see older corporations try to capture millennial’s attention by creating memes or gifs, and just generally trying to be a part of internet culture. It feels so forced and unoriginal that we hardly even bother with those kinds of brands anymore. #GIRLBOSS taught me to break the rules, use your own tone, and stay true to who you are while solving a problem that someone has yet to fix.


Jean: What are your “5 Lessons I Learned as a Twentysomething Founder” and why? Please share a story or example for each.

1. Only create a business with people you have successfully worked with or have worked for during the startup stage: My first startup was and still is incredibly unorganized. I basically just agreed to do it because I had experience in the field and thought it would be cool to be a 23-year-old founder. In the beginning, we were all inexperienced, greedy, and caught up in being founders more so than running a successful business. It took cutting people out, bringing them back in, setting rules, getting in arguments, bootstrapping, and a lot of awkward conversations to get to the point of acquisition. I know now that the people I founded that startup with I will never work with again, and if they’re reading this, they’re probably thinking the same thing about me. I wanted to implement corporate rules and regulations, and they wanted to just coast and hope things fell into place. I liked being organized and to-the-point, whereas they wanted to get rich quick. I had never worked with either of them before, so I had no idea what their skillsets were or how hard they actually did work. We all had to become self-taught in everything we did, which was amazing to see us all choose what we’re good at (or what we think we’re good at), and then run with it. It did, however, make us reluctant to tell each other if we were unhappy with each other’s work because we knew that that person was still learning.

My co-founder today for my second startup has worked both with me and for me. I’ve seen her receive several awards for her work-ethic outside of our professional relationship, and she happens to be one of my closest friends with whom I share many similar ideas. We can bounce back and forth off of each other and are continually coming up with new and authentic ideas for our current startup, and projects we hope to launch in the future.

2. If you lack a skill, teach it to yourself: No one prepares you for the things you have to do when you start a business. You don’t realize that every single thing costs money, right down to the images on your website. Since I’ve started my own business, I’ve become a jack of all trades and master of none. I’ve dabbled in graphic design, social media management, photography, copywriting, content writing, SEO, HTML, negotiating, pitching, creating a deck, branding, marketing, blogging, videography, creating presentations, sales, public speaking, and literally every single thing I never received an education for. If it had to be done, I looked it up and read about it until I could practice it myself. I’ve had at least five years of experience in practicing all of these skills, and the progress shows. I could have gone to school for a few of these skills, but instead, I decided to learn a little bit about each of them, give each a shot, network, and then bring someone else in when I just couldn’t get the finished product I was going for.

3. Make everything legal and organized immediately: This is self-explanatory, but you’d be surprised at what people think they can get away with on the legal front. Do not take any risks. Spend $100 on a lawyer from Upwork and get their counsel. Figure out shares and company percentages before you start making revenue. Get your business license. Get your business account. Do not ever put these things on the back burner and do not let the awkwardness of dividing things up get in the way. You will absolutely pay the price later if you wait on that. And by that time, you will have lost far more than money. You will have failed relationships and discredit your own reputation.

4. Don’t walk on eggshells, ever: If you don’t like something say it. If you don’t have time to do something, don’t. If it’s not essential to the company at that moment, put it off. Getting caught up in the yes’s will just cause a mess.

5. Do not glamorize being busy: 16-hour work days are not sexy. Not having a work/life balance is also not sexy. If you’re constantly busy with work, there’s a good chance you’re not putting out quality work. Take a step break, go on a walk or a vacation, and then come back refreshed so you can put your best foot forward. If you’re regularly boasting about how busy you are with work, you just sound like an asshole that only cares about work. Being a founder doesn’t have to be just that. New ideas and visions come from being in a different environment, and if yours is continuously in the workplace, you’re going to hit a wall.

Jean: Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might see this. 🙂

Whenever I’m feeling lost or unmotivated, I listen to several podcasts like Masters of Scale, Girlboss Radio, the Tim Ferriss Show, The Joe Rogan Experience, Guys We F*cked, etc. All of their guests are fascinating to me, but I find that we all have a very similar thought process, which makes me feel good about my future. While I am continually learning from these hosts and their guests, it’s imperative for me to step outside of what I want and put myself in situations where I am uncomfortable so I can be challenged. Why else would I live in China? That said, I’d have to go with someone I hate, like Donald Trump. Personally, the thought of sharing a meal with him makes my stomach turn, but he is where he is for some strange reason. I want to find a different perspective through his views and hope that I could also persuade him to think differently. I imagine most people would find that to be a lost cause, but I can not imagine a situation where I don’t leave that transaction learning something new about myself, which is ultimately the most valuable lesson when starting a business — knowing who you are.

— Published on June 27, 2018

Originally published at medium.com

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