Ev Williams and His Advice for 20-Somethings

Last year, my best friend Michael and I started a podcast called InTheir20s.

We created our podcast as a way to share professional & career development advice from influential business leaders, celebrities, and all-star athletes. During the pandemic, many of our friends and peers were struggling to find jobs and purpose which is why we have turned to the most influential people in the world about how they have overcome uncertainty and achieved success. In this time of uncertainty, listening to each of our guest’s journeys to impact in their respective fields has been exceptionally informative and inspiring.

Some of our notable guests: Jason Calacanis, Beto O’Rourke, Tim Hardaway Sr, Cathy Bessant, Jewel Burks, AJ Vaynerchuk, Ruben Harris, Sekou Kaalund, and most recently Ev Williams.

My co-host, Michael, passed away on April 20, 2021 after a battle with brain cancer. I’m committed to keeping his memory alive through the podcast we started together.

Interviewing Ev Williams was a pivotal moment in the growth of our platform. Writing about it on Medium, the company Ev founded, is even more rewarding.

Williams has revolutionized the internet as we’ve come to know it. With Blogger, he made blogging accessible to everyone; with Twitter, he helped people share ideas from anywhere; and with Medium, Williams has created a digital network of curious minds. Williams has been instrumental in giving people a voice on the internet. And even with all his accomplishments, Williams sees no reason to stop creating.

Williams fell in love with the internet in his 20s and never looked back.

Growing up on a small farm in Clarks, Nebraska, many would not have expected Williams’ global impact on the Digital Age. After discovering the 2nd-ever edition of Wired Magazine at a local mall in his early 20s, Williams was inspired to make his mark on the cyberspace.

The rest is history.

Here are the top three moments from my interview with Ev Williams:

Learn from Failure

In his life, Williams has reached heights of business acumen that only few will ever see. He sold Blogger to Google at age 31; helped build Twitter into a platform with over 330 Million users; and started Medium, which has the power to become the largest online publishing platform.

Williams endured failures that helped him become a wiser entrepreneur.

Before moving out West, Williams started his first internet company while in Lincoln, Nebraska. From this company, he learned how to build websites and software products. One of the “toughest pills to swallow in his life” was dealing with the early failures of his Nebraska internet company. Williams was forced to fire many of his friends that worked for him and lost money that his father had invested into the company.

After his first year in the Bay Area, Williams started a company called Pyra Labs (Blogger was built as a side-project for Pyra Labs). After Pyra Labs’ first round of funding, the dot com bust occurred. Williams was unable to raise additional funds and was forced to let members of his team go, much like his previous company. During our interview, he mentioned this period of financial hardship was another hit to his self-esteem. Williams was candid about memories spending hours combing through couches for spare change just to be able to afford a cup of coffee.

These moments taught Williams how to “work through failure.”

By working through failure and continuing to create companies, Williams was able to learn from his prior mistakes and plan for the future.

Stay Focused

I asked Ev, What is a common practice you developed in your 20s that has guided you towards success?

His answer: Focus

Many people are aware of the power of focus, but find it challenging to harness it for themselves. During our interview, Williams shared that at times, even he has difficulties focusing.

With so many distractions, one of the most important skills entrepreneurs must possess is focus. Williams recommends younger entrepreneurs find a very small part of a market, or a specific use case, and focus solely on that.

“Don’t try to do too many things, too early.”

Williams believes that many people are discouraged from focusing because they might feel self-conscious about their work. Meaning, if an entrepreneur is focused on solving too small of a problem in a marketplace, they may feel that they are not contributing to the world as they should, or that their work isn’t “exciting enough.” Williams wants more entrepreneurs to push through that feeling of doubt. “Narrowing your focus at first allows you to expand your focus later.”

Always Choose Growth Over Status

In 2017, Williams was invited by the University of Nebraska-Lincoln to be the Commencement speaker, in addition to receiving an honorary degree.

In his 15-minute speech, Williams spoke about the most important lesson he wish he gave himself in his 20s: “choosing growth over status.”

Growing up in Clarks, Nebraska, there was a lot of pressure for Williams to follow a specific path in life. In his hometown, many people achieved status by excelling in sports, particularly football, or through material wealth. Williams found it difficult to align with this culture, and often felt like an outsider.

Williams ultimately dropped out of college because he was anxious to get out into the world and find external validation through entrepreneurship.

During our discussion, Williams shared that there were many moments in his youth where he felt he was in a rush to prove himself. By focusing on his growth as an entrepreneur instead of his status, Williams may have made more progress sooner if he was focused on his development and progress, rather than what he was achieving.

Growth is directly tied to patience.

Williams has observed many people that are too pressed on getting a better title or managing more people, when instead they should be patient with their progress and focus more on the day-to-day. In the long-term, people who focus on their growth early in their career find more success later down the line.

Stream InTheir20s on Spotify, Apple Podcasts, & YouTube for the best advice from the best people. Learn more at www.intheir20s.com

Quick Background on Tim Hardaway Sr.

Tim Hardaway Sr. is a former professional basketball player who played for five different teams during his tenure in the NBA. Hardaway Sr. was a 5 time All Star and known for his killer crossover, along with the joy he played the game with. He had the honor of going up against many all time greats including Micheal Jordan, Karl Malone, Magic Johnson and other prolific stars. Recently, Landon and Michael had the chance to sit down with Hardaway Sr. to ask about his NBA career and hear his advice for young athletes in their 20’s currently.

Patience

One habit Hardaway Sr. advises younger athletes to develop was patience. Many times, young athletes declare themselves for the draft after 1 or 2 years in college, and ultimately suffer from their decision for the rest of their career. Instead of declaring for the draft after a year, he advises young athletes to continue developing their on-the-court game, while finishing their education. The key of patience does not just apply to student athletes but can be true for anyone.

For the longest time, I had no idea what I wanted to do with the rest of my career but I stayed patient and kept exploring different career paths rather than making a haste decision and choosing a career that I would not be passionate about. I also learned early that when it comes to investing in the stock market, the biggest difference between someone who makes money versus someone who loses money is how much patience they show while investing.

Self Confidence

Another skill that Hardaway Sr. believes is very important for young people is having self confidence. In the NBA, there are many talented individuals, which means it could take some time before many players get an opportunity to play. People shouldn’t lose confidence in themselves if this happens, because instead they should keep working hard and stay ready for their opportunity to showcase their skills.

During the pandemic, many Gen Z’s lost their jobs and have been in a downward spiral ever since. After listening to this podcast, my recommendation to all these people would be to keep believing in yourself and keep learning new skills that will make you a more attractive candidate to employers. If you do not believe in your talents, then nobody else is going to believe in you. Confidence is the most beautiful thing one can possess. Hardaway Sr. gave Michael and Landon some great advice about having confidence in themselves and to ignore anyone who hates on what they’re trying to accomplish. From the minute Hardaway Sr started playing basketball, he had people telling him he was too small for the NBA, but by believing in himself and his talents, he was able to have an amazing career and accomplish all of his goals.

Save Money and Stay Smart

The last piece of advice Hardaway Sr. gave young athletes was to save money and always think ahead. With any sport, you can have a limited career, which means you should have a plan to save money from the beginning. Over time, we’ve seen so many instances of professional athletes and wealthy entrepreneurs lose money and end up struggling financially for the rest of their lives. Even if you are in the beginning in your 20s, it is never too early to begin saving for retirement. Everyone should start saving early so they can be prepared for a rainy day.

Mia McManus, a student and Winter Intern for InTheir20s shares her thoughts on our recent interview with Amir Badr

Quick Background on Amir Badr

In this interview, Amir Badr identified his desire to leave his home country of Iran at the young age of seventeen years old. However, all of the odds were against Badr when he discovered that only a two-year military term could satisfy this desire. Despite this, Badr was able to successfully escape Iran without serving a military term due to his own grandmother. Funding totaling to an amount of five thousand dollars from his grandmother fueled his escape. He then ventured to Turkey, Germany, and ultimately the United States of America. Badr arrived at an airport not knowing a word of English, having only an address and one hundred dollars. A kind stranger noticed that he was lost and helped him by offering directions and a paid taxi ride. A few months later, Badr ran into the same kind stranger from the airport at his job at a Persian Mediterranean restaurant. The two reconnected and this kind individual soon became his mentor, who eventually landed him a competitive job at Exelon.

Motivation behind Upkey

The birth of Upkey resulted from Badr noticing that many immigrants and minorities in the United States do not have professional resources, and often struggle to map out their academic and professional journeys. Keeping this in mind, he created Upkey to provide mentorships, externships, networking, and skill development in an interactive way. Resulting in a population of current students and recent graduates who will be prepared when transitioning into the job market. Badr also came across the issue of many Fortune 500 companies not recruiting diverse candidate pools. This resulted in companies only selecting candidates from top schools and universities that are considered to be “a perfect fit”. Upkey strives to break down this barrier on a daily basis by encouraging recruiters to expand their company’s candidate pool by looking beyond an individual’s grade point average and socioeconomic background. In return, this creates value in the grit, perseverance, and personality of individuals.

The Start of the Virtual Internship Program

Over 10,000 students expressed to Amir that they lost their internship due to the pandemic. The students also mentioned that they were not sure how they were going to advance in their professional endeavors in the midst of a pandemic crisis. This prompted Badr to create Upkey’s signature program that was launched during the start of the pandemic in the summer of 2020. The virtual internship fostered a learning experience for both Upkey Interns and staff members. Approximately 1,000 interns were introduced to a curriculum that focused on high demand twenty-first-century skills. Such as consulting, finance, artificial intelligence, communication, and leadership to name a few. Upkey used this program to fulfill the needs of a diverse array of students and this is displayed in their data. For example, sixty percent of these students were classified as minorities. Not to mention that fifty-two percent of these students were first-generation college students.

My first thoughts when choosing which interview to review were, “Which one relates to me the most?” Then I saw this one. I thought to myself, this seems like one I could benefit from because I had just taken a management course in school where we had discussed company culture.

InTheir20s interviewed Kati Quigley, Senior Director of Global Industry Marketing at Microsoft. With over 20 years of experience under her belt, I figured her interview would be the most beneficial and exciting to watch. My favorite thing about Kati was that our interests align as well. I plan to major in marketing, while she is a director for at Microsoft. We also both enjoy event planning and execution.

My favorite takeaway from this interview, however, has to be Quigley’s view of company administrators.

I got my first job just under 4 months ago. I work 2 part-time jobs, both in retail. When applying for the first one, I heard countless adults tell me how to structure my resume and what to say or not to say during the interview. As someone who gets nervous during interviews, it was pretty nerve-wracking to hear all these different views on what the right way to act is. In the end, I went with the cliche saying of “being myself.” That and projecting myself as the perfect candidate for the job. My resume included the clubs I was in, the classes I had taken, and my grades. The interesting part is that none of those related to a retail job. I identified with Kati when she shared a story about interns Microsoft hired in the past. The interns had plenty of experience, but not in computer software. Each intern or college hire that got an interview was engaged in non-academic activities that highlighted their passions. Sometimes the passion related to the job, and sometimes it was unrelated. Various activities such as participating in sports, founding nonprofits, and working for smaller companies all contributed to their character and increased their chances of being hired. I plan to integrate this advice into my business life by adjusting my resume so that the irrelevant activities are gone and only my passions/relevant experience is listed.

The second most interesting piece of advice I heard was to interview the company back. At first I didn’t understand what she meant, but as the interview continued, it was shocking how right Kati was. Her take on interviews is that so many people worry about presenting themselves as the right candidate for the job without taking time to realize if the company is one they can picture themselves in. It’s like walking into a restaurant but not realizing their seating is uncomfortable and their food isn’t your preference. It might be a great restaurant and you want to eat there because of the great reviews, but it’s not the right one for your taste buds. Next time you’re at an interview, don’t be afraid to ask them questions as well. Figure out if their company culture is one you can imagine yourself being apart of; figure out if their company values are one’s you can align yourself with. Another common misconception: curiosity equals lack of knowledge. Honestly, I used to think the same before watching Kati’s interview, but after listening to her explain it, I see it’s a valued quality. Many avoid asking too many questions because it might seem as if they are uneducated about the position when in reality, it shows interest and allows them to get a feel for the company. When interviewing for a larger company in the future, I know I’ll definitely remember this. Right now, it’s my dream to intern at Pinterest. However, I’ll get a feel for what the employee environment is like and the company culture. And you should, too.

The last piece of advice was something I’ve never heard of before. It’s probably because I haven’t been in the business world for very long, but Kati described it perfectly. Landon asked her when she was a recent college grad, which did she work to achieve: vertical or horizontal growth? Her response was both. Vertical growth pertains to “climbing the ladder,” or seeking promotion after promotion. Horizontal growth would get a feel for where you are while staying at your current level. Kati responded that out of college, she focused on both. However, she recommended horizontal first just because of the change you need to make to a company before thinking about promotions. What interested me the most about this concept was that she described multiple “turns” she made, all of which were horizontal. She may have joined a new company with the same position or learned new skills without leveling up. In her experience, it’s unlikely to make a vertical and horizontal shift simultaneously, Regardless, any shift is good because it represents progress. And progress is success.

Our podcast went live on June 15, 2020 because we saw the need to help students and young professionals, who like us, graduated during a global pandemic.

In what continues to be an odd and isolating time, young people have less and less resources for inspiration. It was because of this, we built a podcast that seeks interviews with influential Biz Leaders, Celebrities, and All-Star Athletes to hear how they navigated the travails and opportunities during their 20s, while gaining an in-depth look into the strategies that led them towards success.

When we launched InTheir20s, we could’ve never imagined that our “quarantine idea” would evolve into something that’s really impacting the lives of a lot of people during the pandemic.

Over the past few months, we’ve had many great conversations with influential people on our podcast like Presidential candidates, celebrity chefs, Hall-of-Fame athletes, well-recognized doctors, and Fortune 500 CEO’s. In a few weeks, we’ll be releasing episodes with ‘The Most Powerful Woman in Banking’ and a cast member from MTV’s Wild N’ Out. Our goal has remained the same since we began: Share the best advice with students and young professionals.

We recently sat down with Amir Badr, the Founder and CEO of Upkey. Upkey is a career development startup based in Chicago, IL that helps students prepare for the professional world by helping them get noticed by top companies. Upkey does this by utilizing their proprietary suite of software tools to help companies remove traditional hiring biases with students.

The story of how Amir developed Upkey dates back to his early days. When Amir was 17 years old, he fled his home country of Iran to begin a new journey in America. He had zero connections and no professional network. And then, on a lucky encounter in the airport, Amir met his very first mentor, who would change his life and guide him through the professional world. Amir’s mission with Upkey is to recreate that “airport scene” for students and young professionals, through virtual mentoring opportunities and career-readiness tools.

Our interview with Amir was both eye-opening and inspirational. It became clear that our missions were aligned, and that we could work together to help students and young professionals by providing them with the tools needed to succeed.

We’re excited to share that we’ve partnered with Upkey to bring 10 passionate college students onboard to the InTheir20s Podcast team as apart of a Virtual Internship Program.

Our internship will focus on four fundamental roles: Podcasting, Social Media Marketing, Content Creation, and Business Development. Our unique program will help students gain impactful experience outside of the classroom; build a network of useful connections; and find work they are truly passionate about. We‘ll share updates over the next few weeks about what our interns are up to and how their internship has expanded both their tool box skills and outlooks.

For anyone in their twenties with an idea, start small and dream big. You never know where your ideas can take you. All you need is a plan and purpose.

Make sure to follow In Their 20s and Upkey for updates on our internship. Don’t forget to stream our podcast @intheir20s

In this time of uncertainty, we felt it’d be a useful tool for Generation Z to hear from successful business leaders about how they overcame adversity in their 20s.

On our podcast, we interview influential leaders to hear about the risks they took and mistakes they made that led to the success stories of their 20s. We’ve shared over 40 interviews with individuals that have seen great achievements in their professional careers.

Colin McMahon

Editor-in-Chief of the Chicago Tribune

“Don’t allow rejection to knock you off your game.”

After graduating from college, Colin McMahon felt he was qualified to apply to a handful of well-known newspaper companies. He recounts one interview in particular with the Baltimore Sun, which at the time was one of the top newspaper companies in the country. Colin was completely shot down by the recruiter, being told that he was unqualified and not ready to join their company. Colin’s felt crushed after this rejection, but he knew he couldn’t give up.

After reflecting on his own accomplishments and career aspirations, McMahon was able to understand that this rejection wasn’t the end of the world.

“This rejection didn’t defy my job search or skills as a journalist. For all I knew, the recruiter could’ve been having a bad day. I knew I couldn’t give up after one rejection.”

Shortly after, Colin was introduced to an individual at the Chicago Tribune and ended up accepting a position with the company. A few months into his career with the Tribune, the Baltimore Sun reached out to Colin to see if he’d be interested in leaving the Tribune to work at the Sun. Colin declined the Sun’s interest and continued his career at the Tribune, where he is now the Editor-in-Chief.

“I don’t like to say everything happens for a reason, but I do like looking at where I am in my life to look back at things that originally didn’t go my way. What if the Sun never rejected me? What if I left the Tribune? Would my life be better or worse? I for sure wouldn’t be where I am today.”

Jewel Burks

Head of Google for Startups — US

“Understand your strengths and weaknesses, in order to find the right people to help you succeed.”

Early on, Jewel Burks always knew she wanted to become an entrepreneur. While taking MBA prep courses, she came up with an idea for a company that she began to focus in on. There was a point when she had to make a tough decision between continuing to get her MBA or turning her idea into a company. Jewel decided to pursue her company, PartPic, which she successfully built and sold to Amazon in her 20s.

Jewel shared that while launching her company, her biggest roadblock was trying to create PartPic with zero tech experience. She didn’t let this stop her.

Burks knew she had to surround herself with people who could help her understand more about engineering and technology. She began to spend time with engineering students at her school, from who she could learn. Jewel understood early that she didn’t have the skills or experience to bring her vision to life, which is why she knew she had to find the right people to work with.

Jewel didn’t let her marketing degree stop her from creating a tech company. Instead, she found people with the skills necessary to help build her company.

AJ Vaynerchuk

Co-Founder of VaynerMedia and CEO of VaynerSports

“Managing burnout in your 20s is crucial.”

At 22 years old, AJ Vaynerchuk co-founded VaynerMedia; by 25, he managed 40 people and 300 employees; and by 26 he had four years of agency experience. AJ was able to build and grow his company to a $100 million dollar agency, all while in his 20s.

Regardless of his early success, VaynerMedia’s rapid growth left AJ feeling burned out in his 20s.

Vaynerchuk decided to give therapy a chance, in order to help him learn how to balance his work and personal life in a more efficient way.

“You have to focus on the human mind in order to solve burn out.”

From therapy, AJ discovered that there is a defensive and offensive side of the human mind. Therapy can help those struggling with getting back to even on their defensive side, but finding other resources to assist with mental strength on the offensive side is equally as important.

These offensive tools can include:

1. Exercising
2. Eating a balanced diet
3. Improving your sleep habits

Effective career advice is an important asset because it helps point young people in a direction towards success.

We need to share more stories of how successful people got to where they are today, in order to inspire the next movers and shakers of the professional world. Colin McMahon, Jewel Burks, and AJ Vaynerchuk got to where they are today by remaining resilient, thinking outside the box, and utilizing resources in the workplace. These are three crucial skills that will help YOU become successful.

Stream In Their 20s on Spotify, Apple Podcasts, & YouTube to be inspired. Learn more about their mission at www.intheir20s.com

The 20s are the most important time in your life to “figure it out.” We all have so many questions about what we should be doing at this point in our lives

In Their 20s provides viewers with a network of influential people, who already went through the struggles of their 20s.

So far, they’ve had over 20 interviews with Business Leaders, Doctors, NBA Legends, Designers, and even 2020 Presidential candidate Beto O’Rourke

Each of their interviews are vastly different. When it comes to their selection process, they work towards sharing unique stories and diverse backgrounds so that their audience can connect with the stories they share.

In Their 20s shares the best advice from the best people!

Here are some memorable moments from their favorite interviews:

1. Ask more “why” questions than “how” questions

While interviewing Dennis Bautista, the VP of Data Analytics at HUB International, Dennis shared how young professionals need to ask more “why” questions instead of “how” questions. He explains how young people must become more comfortable with challenging the status quo during their daily lives.

Doing this can help accelerate your ability to learn, while also helping you stand out. Being naturally curious is one of the best assets a young professional can have.

Interview with Dennis Bautista

2. Be forward thinking

During their interview with Kati Quigley, the Senior Director of Global Industry Marketing at Microsoft, Kati spoke about the importance of being a forward thinking individual.

“Work hard and do whatever it takes to get the experience you need; network with your peers — as you grow in your career, they will be the ones that you continue to rely on and connect with through the years; find something you love and find energy doing; and build your career on your strengths because you are in it for long term, not short term,” Kati said.

You should always be actively planning for your future, while taking care of your day-to-day responsibilities. This will help you become a forward thinker.

Interview with Kati Quigley

3. Find the things you love in your 20s

Landon and Michal had an opportunity to interview Kevin Coval, who is the Artistic Director of Young Chicago Authors and also the mentor of Chance the Rapper. He shared with the duo that your 20s are the best years to find the things you want to do.

“[The 20s] are about exploring, picking something up, investing in it, and becoming a nerd about it. Trying new things gives you an opportunity to also find the things you don’t love doing. This will save you time in the future.”

Use your 20s to explore multiple passions in order to find ones that you truly love doing.

Interview with Kevin Coval

4. Your network is your net worth

During their interview with Dawn Dickson, the Founder of POPCOM, Dawn shared a memorable quote with us that stands out to this day:

“You Network is Your Net Worth”

What this means is that you need to surround yourself with people who will help you grow and motivate you to do well. Some people hate it, some people love it, but at least we can all agree: Networking is one of the most important business skills that one can posses.

With this being said, you must put time aside to invest in your relationships with others.

Interview with Dawn Dickson

5. Don’t slack off during internships

During their interview with Steve Stoute, the current Chief of Staff of DePaul University in Chicago, Steve spoke with Landon and Michael about the importance of accountability and hard work while at your internship.

“There’s no room to slack off [during an internship]. Work to the best of your ability to perform well. Give it everything you have. Everyday. You never know what other opportunities may come out of your internship,” Steve says.

While at your internship, you only get a few chances to showcase your skills and prove to the company that you’re willing to work hard and absorb knowledge. Work hard and represent yourself everyday.

Interview with Steve Stoute

Everybody in their 20s deserves access to the best advice on the planet.

In a time of uncertainty, In Their 20s is Landon and Michael’s best attempt of sharing important content that can help our peers navigate their 20s. The Co-Hosts believe that in order to be successful, you need to see success.

Subscribe to In Their 20s on YouTube to be inspired. Learn more about their mission at www.intheir20s.com

Michael and I created In Their 20s to share the best advice and success stories with our friends and peers. Our list of influential people include CEOs, Doctors, Business Leaders, Celebrity Chefs, Fashion Designers, NBA Legends, Poets, and even 2020 Presidential candidate Beto O’Rourke.

We’re humbled to have had an opportunity to interview Beto O’Rourke, considering how influential he is to not only people in their 20s, but to people of all ages.

Beto is a super genuine guy, and he even went much longer than the time we were expecting to have with him. We asked him some very authentic questions about his 20s, and he shared with us some of the best advice he had for people in their 20s.

Here are the best lessons we learned from our interview with Beto O’Rourke:

1. Have multiple passions in your 20s

Beto O’Rourke was in a band in his 20s, where he was able to create some of the best memories of his life. Beto enjoyed playing music with his friends, and even considers music to be whole another language.

In a candid moment, Beto reflects on how difficult it is to continue having a passion like music while juggling other important adult responsibilities. He longs for the experience of collaboration in musical creation with his friends, but also realizes how difficult it can be to organize “jam sessions” with his old band buddies.

“If you are free of responsibilities and a level of accountability [in your 20s], you should always choose to pursue a passion. As you get older, it’s difficult to find the same amount of time for your passions”

He recommends giving yourself permission to set off on an unexpected path in your 20s because there are less penalties for pursuing passions while you’re young.

2. Take as many risks as you can in your 20s

In the beginning of our interview, Beto shared how he’s seen so many people squander at the opportunity to take risks and chances in their 20s because they are too comfortable with a certain lifestyle and routine. He feels that people on a specific track in life are less likely to take risks and try new things.

“The balance of taking risks and getting high reward is much easier to strike while you’re in your 20s”

With this in mind, it may be more difficult to take a risk when you’re out of your 20s, due to the fact that you may have more responsibilities.

“If you don’t expose yourself to enough life perspectives and risks you’ll become a very narrow person”

3. Develop a strong work ethic in your 20s

In college, Beto had to quickly learn how to juggle schoolwork, a job, and a varsity sport. With the exception of some of his recent campaigns, he shared with us how his college years were some of the most exhausting years of his life. Beto credits his strong work ethic to the time he spent multitasking while in college. In his 20s, Beto O’Rourke learned the value of hard work.

“When you’re in your 20s, your mom isn’t around to wake you up and tell you to go to work or tell you what the consequences will be if you don’t.”

When it comes to hiring people to work on his recent campaigns and organizations, Beto rarely looks for people who will be the most proficient at the job, instead he looks for people who are able to “work their heart out.”

4. It’s okay to make mistakes in your 20s

Making mistakes in your 20s is always healthy. Mistakes lend people with opportunities to learn about who they are, and how to put themselves in a better place for the future. While speaking about mistakes, Beto shared a very interesting quote that went something like this:

“In your 20s, know who you are and learn who you aren’t”

You don’t learn much from doing things “the right way”, instead you learn through making mistakes. This is a crucial lesson for people in their 20s to remember.

Overall, Michael and I really enjoyed having Beto O’Rourke on our web-series. He shared great advice that people in their 20s can benefit a lot from hearing. The whole objective of In Their 20s is to share the teachings and lessons of influential people for everybody to hear. We were very thankful to have had the opportunity to host someone as influential as Beto O’Rourke on In Their 20s.

Watch our full interview with Beto O’Rourke on YouTube at In Their 20s and Learn more at www.intheir20s.com

In college, I was often searching for ways to apply my classroom teachings to the real world. I felt that by putting what I had
already learned in the classroom to work, I’d be able to find the most value while in college.

I had a bunch of internships, but I was still hungry for more unique experiences. This is when I came up with the idea to do freelance work for any business that would give me a shot…

Getting a small business to pay for my freelancing abilities was a challenge. I knocked on the doors of many small businesses and received many no’s. These businesses included coffee shops, sporting good stores, restaurants, clothing stores, and bars.

Through rejection, it was clear that I had to redefine my pitch to small business owners. I had to create stronger proposition for why these small business owners would want my help. This meant I had to find solutions to their unique problems. I did this by asking a whole lot of questions.

Every small business is different, which means they might each undergo a unique set of problems. As a freelance worker, you need to understand their unique challenges, in order to understand how to fix them.

Here are some of the questions I began to ask small business owners:

1. What is your target customer?
2. How do most of your customers find out about your business and offerings?
3. Are you currently running any promotions with college students?
4. How much business are you seeing come through the door? How does it fluctuate by day of week?
5. How is your social media presence?
6. Are you willing to try out new and creative campaigns to drive sales?
7. How much money have you spent on marketing?
8. Do you have any competitors in the area? If so, what are they doing better?

With my new approach, small businesses began to become more interested in meeting with me because they saw how I was actively interested in solving their unique challenges.

My persistence paid off and I was able to connect with the owner of a sports pub near my college campus. The pub, Tobacco Road Tap Room, happens to be the first Chicago sports pub to affiliate itself with an entire collegiate athletic conference. During our conversations, we both saw how our ideas for Tobacco Road’s future were heavily aligned. He needed help driving foot traffic, boosting online presence, and creating event engagement. These were all things I knew I could help him succeed with.

After our initial conversation, I told him I’d return in a week with a PowerPoint presentation outlining specifically what I’d bring to the table. My presentation would layout his problems, my solutions, and why I was best equipped for the job. This helped him clearly see how he’d get a return on investment by hiring me as a freelance worker. Always layout your plan.

He ended up hiring me and I worked with Tobacco Road for over a year. My freelance role evolved over time, and I had opportunities to work on some very interesting projects.

Here are some of the things I did for Tobacco Road:

1. Deployed interactive marketing campaigns that increased foot traffic exponentially.
2. Helped Tobacco Road connect more effectively with 21+ college students for events.
3. Ran Tobacco Road’s social media and online advertising across all social platforms.
4. Created unique specials and day-of-week deals for customers.
5. Developed video promos and visual content that helped Tobacco Road trend within the community.
6. Marketed events like: live band karaoke night, concert ticket raffles, and mechanical bull nights.

Overall, he was very satisfied with my freelance work because I was able to deliver strong results for Tobacco Road. I did this by understanding his challenges, creating monthly metrics, and meeting with him often to see if new challenges arose and how I could help solve them. In addition, the responsibilities of freelance work gave me unique experiences that I wouldn’t have received elsewhere.

Everyone wants to do freelance work, but how do you actually get hired?

1. Have a Presence — Ask Questions and Be Engaged.
2. Have a Passion — Show small business owners that you‘re passionate about what you do.
3. Have a Plan — Come to meetings prepared with a plan of how you will solve their unique problems.

Small business owners want to know whether or not you’re able to help solve their challenges, in order to help their business grow. Freelance work is problem-solving.

Stream In Their 20s on Spotify, Apple Podcasts, & YouTube to be inspired. Learn more about their mission at www.intheir20s.com

In college, I was often searching for ways to apply my classroom teachings to the real world. I felt that by putting what I had
already learned in the classroom to work, I’d be able to find the most value while in college.

I had a bunch of internships, but I was still hungry for more unique experiences. This is when I came up with the idea to do freelance work for any business that would give me a shot…

Getting a small business to pay for my freelancing abilities was a challenge. I knocked on the doors of many small businesses and received many no’s. These businesses included coffee shops, sporting good stores, restaurants, clothing stores, and bars.

Through rejection, it was clear that I had to redefine my pitch to small business owners. I had to create stronger proposition for why these small business owners would want my help. This meant I had to find solutions to their unique problems. I did this by asking a whole lot of questions.

Every small business is different, which means they might each undergo a unique set of problems. As a freelance worker, you need to understand their unique challenges, in order to understand how to fix them.

Here are some of the questions I began to ask small business owners:

1. What is your target customer?
2. How do most of your customers find out about your business and offerings?
3. Are you currently running any promotions with college students?
4. How much business are you seeing come through the door? How does it fluctuate by day of week?
5. How is your social media presence?
6. Are you willing to try out new and creative campaigns to drive sales?
7. How much money have you spent on marketing?
8. Do you have any competitors in the area? If so, what are they doing better?

With my new approach, small businesses began to become more interested in meeting with me because they saw how I was actively interested in solving their unique challenges.

My persistence paid off and I was able to connect with the owner of a sports pub near my college campus. The pub, Tobacco Road Tap Room, happens to be the first Chicago sports pub to affiliate itself with an entire collegiate athletic conference. During our conversations, we both saw how our ideas for Tobacco Road’s future were heavily aligned. He needed help driving foot traffic, boosting online presence, and creating event engagement. These were all things I knew I could help him succeed with.

After our initial conversation, I told him I’d return in a week with a PowerPoint presentation outlining specifically what I’d bring to the table. My presentation would layout his problems, my solutions, and why I was best equipped for the job. This helped him clearly see how he’d get a return on investment by hiring me as a freelance worker. Always layout your plan.

He ended up hiring me and I worked with Tobacco Road for over a year. My freelance role evolved over time, and I had opportunities to work on some very interesting projects.

Here are some of the things I did for Tobacco Road:

1. Deployed interactive marketing campaigns that increased foot traffic exponentially.
2. Helped Tobacco Road connect more effectively with 21+ college students for events.
3. Ran Tobacco Road’s social media and online advertising across all social platforms.
4. Created unique specials and day-of-week deals for customers.
5. Developed video promos and visual content that helped Tobacco Road trend within the community.
6. Marketed events like: live band karaoke night, concert ticket raffles, and mechanical bull nights.

Overall, he was very satisfied with my freelance work because I was able to deliver strong results for Tobacco Road. I did this by understanding his challenges, creating monthly metrics, and meeting with him often to see if new challenges arose and how I could help solve them. In addition, the responsibilities of freelance work gave me unique experiences that I wouldn’t have received elsewhere.

Everyone wants to do freelance work, but how do you actually get hired?

1. Have a Presence — Ask Questions and Be Engaged.
2. Have a Passion — Show small business owners that you‘re passionate about what you do.
3. Have a Plan — Come to meetings prepared with a plan of how you will solve their unique problems.

Small business owners want to know whether or not you’re able to help solve their challenges, in order to help their business grow. Freelance work is problem-solving.

I have a new web-series where I interview influential people to talk about their 20s. Subscribe to In Their 20s on YouTube to get inspired. Learn more about our mission at www.intheir20s.com