By David Lai, 2016 Fellow

Hey there, VFA Blogosphere. Happy Pride!
My name is David, and I’m a 2016 Fellow currently living in LA working in market research & political consulting. During the fellowship, I split my time between Miami, FL and Denver, CO. I went from managing marketing and business development at a fast-casual ceviche restaurant to building out the data science department at an online interior design company.
I was flattered when I was approached to write a blog post for VFA this month for VentureOUT – a resource group for LGBTQ+ Fellows and Alums. The overall topic I was tasked to write about: my experience as an LGBTQ+ fellow in VFA. Pretty broad, right? “Clear as mud” as one of my supervisors used to say during our meetings. In efforts to streamline my thoughts, I’ve decided to focus on three key experiences I’ve had as a VFA Fellow – attending Training Camp and working at startups in Miami and Denver.
These are only my personal experiences. I do not mean to and cannot speak for the entire LGBTQ+ community.

Attending Training Camp

Coming into Training Camp, I knew I wanted to find other queer fellows to connect with. It was particularly important in VFA because I knew I would be going to cities that weren’t what I would typically deem as “gay meccas” like NYC, SF, and LA. I falsely bought into the notion of “metronormativity”- that queer people only lived in major cities and nowhere else – and feared that as a queer person of color (QPOC) in a VFA city, I would have a difficult time finding communities of people similar to me.
By the end of Training Camp, some of the queer fellows and I had formed VentureOUT and led a diversity workshop on LGBTQ+ identities for my fellow Fellows. The VFA Team was incredibly supportive in both of these endeavors, and gave me some reassurance that I would continue to be involved in queer communities post-grad.

Starting my Fellowship in Miami

In my first week in Miami, I joined a gay men’s tennis league and ran out of tinder likes much faster than I ever humanly thought possible (we all do this in a new city, no shame). In queer communities, it’s not uncommon to use dating apps to find platonic friends. I had faith that I could make perhaps one or two friends from the app – along with a date or two.

The first couple of months were admittedly rough. It’s hard enough to make friends in a new city, but tack on a preference for a certain sexual identity that approximately only 10% of the general population identifies with, and it just makes it that much harder. But eventually, I had two close QPOC friends that I met on Tinder, and attended a weekly potluck with the gay men’s tennis group.
These queer connections helped me stay sane in Miami, where there was (from my perspective) a rather strict adherence to gender norms. For instance, men were to greet women with a kiss on the cheek and other men with a firm handshake – even in a business context. Although this gendered behavior was rather innocuous, I couldn’t help but wonder what would happen if I greeted another man with a kiss on the cheek in a business setting. I don’t think that action would have been so innocuous.

Moving to Denver

After a year in Miami, I decided to move to Denver for another opportunity within VFA because my interests had shifted from restaurants to data science. I also wanted to get a taste of what other US cities were like from the perspective of VFA, as I believe the cities themselves are perhaps some of VFA’s biggest assets. Similar to Miami, I joined an LGBT group and utilized dating apps to make queer friends – with great success, much to my (pleasant) surprise.

My time in Denver surpassed all my expectations. I never expected to make so many queer friends (from a dating app, no less) who also understood the nuanced ways in which the LGBTQ community discriminates against QPOC. One of my non-POC friends actually almost got into a fist fight when someone threw a racial slur my way at a bar and I was too scared to confront him; although I don’t condone violence, the sentiment was oddly reassuring – I appreciated that he spoke up for me when I did not feel safe doing so myself.
My friends even somehow managed to give me the courage to perform drag for the first time. They helped with everything, from taking me dress shopping, raiding the local Walgreens for cheap makeup, sending me links for heels that might work for my outfit, and going with me to my friend’s party so I wouldn’t be the only one in drag there.
Never in a million years would I have imagined that Miami and Denver could be places I could so deeply explore my queer identity, and connect with so many compassionate queer folk who would support my journey.
Ironically, I did end up moving to Los Angeles – one of the “gay meccas” I had my sights on in the beginning of the fellowship. Towards the end of the fellowship I realized I wanted to engage in advocacy work, primarily for LGBTQ and POC, and Los Angeles had the opportunities I was looking for.

Life Post Fellowship

It certainly feels strange living and working in a non-VFA city; however, even in the City of Angels, I believe the VFA core values still apply. Now more than ever I am determined to create value for myself and others and believe all the more fervently that smart people should build things – especially non-physical “things”.
The term “engineer” has largely been used to describe people building products or software, but rarely has it been used for people who build and tinker with seemingly intangible systems (e.g. referral programs, operational processes, community building). I think we need to start reframing the notion of what an engineer is, especially for VFA fellows. For better or worse, I believe VFA makes us all more of an “engineer” than when we first entered.
Personally, I am interested in figuring out how to engineer the various social, cultural, and political systems that shape our everyday lives to improve these systems for LGBTQ+ and POC communities. In undergrad, studying psychology and sociology, I’d often tell people that I aspired to be a “cultural engineer” or “social architect” without really understanding what those buzzwords really meant. After VFA, I still don’t. But, I do have the courage to more confidently say that I still aspire to those ideals, and the knowledge that I can build a great community of people around me wherever I am to help me figure everything out along the way.

It’s your first week at your first startup job. Amazing, congrats! You know how to do literally everything already, right? Wait, I’m sorry…you don’t?

Well, we’ve got good news and better news: 1) you don’t need to know how to perform every task right away—no one expects that of an entry-level hire. And 2) a little thing called Google exists (maybe you’ve heard of it). Why, though, are we talking about a search engine instead of the human search engine known as your manager? Glad you asked.

You should not rely on your manager to answer every question.

The simple reason? You were hired to take work off of your manager’s plate, not pile more on. Even if your boss does have the answer to every question you can come up with—which is very, very unlikely—responding to your every query is almost certainly not the best use of their time.

Plus: self-sufficiency is a good look. Put yourself in your manager’s shoes. Would you rather have an employee who figured things out pretty much on her own, or one who pummeled you with questions throughout the day?

But how do you decide what to ask, and what to try to figure out on your own? It can be a little tricky at first, but we’ve got you covered.

You should Google if:

You just need to learn a simple skill.

Need to design a simple infographic, but don’t know where to start? Try searching “simple free infographic tool” and be blown away by the bounty of useful platforms and templates on the internet. The same goes for all kinds of skills—if you need to do something quickly, and it doesn’t need to be perfect, teaching yourself is a great option. One caveat: if you know your boss is incredibly particular about the way this task is performed, it might be worth checking in before Googling.

The process doesn’t exist yet. 

Let’s say you’re tasked with unknotting a big, logistical problem your startup faces, and to find a way to prevent that same knot from forming again. Sounds fun! Also sounds like you’re on your own, to some degree. You’ll probably want to ask questions at some point down the line, but do what you can to problem solve on your own first. You were tasked with this job for two reason: other people on the team don’t have the bandwidth and your manager believes you can do it. Have some faith in yourself.

Your boss asked you to figure it out.

This one should be a no-brainer, but it bears repeating. Did your boss ask you to edit a video, because someone needs to do it, he doesn’t know how, and he’s swamped? This is not the time to ask him how to.

You’ve been given this information before.

In this case, you shouldn’t be searching the internet—you should be searching your email account and your own notes. (You’ve been taking notes, right? Good.) If you really, really can’t find the info you need, after an exhaustive search, then you can ask—but do what you can to avoid it, and try to make sure you keep track of information next time.

When to ask questions:

When you need access to a company-specific piece of information, a platform, or a password.

If you can’t continue working without a piece of information that cannot be found on Google, it’s a pretty good time to ask a question.

First, to be safe, take one more pass through your onboarding materials, and see if there might be anything you missed. Was your work email login info sent to your personal account? Is there a password manager where instructions or password are stored?

When you’re making a decision with real consequences.

Debating between several intern candidates? Considering hiring (or firing) a contractor? About to make some big, sweeping changes to the architecture of your company’s website? These are all moments when there’s not necessarily a clear-cut answer—and your manager’s experience would probably help you in a serious way. Asking for input also ensures that you have the buy in and permission to proceed.

When there’s money involved.

If you’re deciding whether or not to buy something for the office, sign up for a platform, or make any other purchase that you haven’t discussed first, it’s worth flagging for your manager.

When you want a gut check on a large, important project.

If you were tasked with a serious, meaty project, like overhauling your company’s website or building out your nonprofit’s annual report, we strongly recommend asking questions early and often. There’s nothing worse than spending weeks completing a project in isolation only to discover that you’ve gone down a wildly wrong path—a pretty common pitfall of entry level startup employees, who are often given a lot of responsibility and minimal oversight.

Okay, so you need to ask for help? Consider this approach.

When possible, ask a peer first.

If the question is something that anyone on your staff might know, consider asking a more junior member of the team first. Again, your job is to take work off of your manager’s plate and free up their time. So try to ask the most junior person who likely has the answer. Sure, the CEO probably does know where the extra paper for the printer is stored, but the operations associate does too. Asking a peer will save you a conversation with your manager, and it’s not a bad way to make a friend. Just make sure that when the opportunity presents itself, you find a way to be just as helpful as the colleagues who gave you a hand.

Try to save questions for a regularly scheduled check-in.

If you have a check-in with your manager every week, see if you can save up your questions until that time—it will be more efficient and less distracting for your manager if she can tackle all of these needs at once. Plus, if you’ve been keeping careful track of the information you need, it will make you look conscientious and detail-oriented.

When is it ok to ask on the spot?

You need this question answered before you can do any other work.

Have you exhausted the tasks you can complete without this piece of information, and exhausted your search? Okay, go ahead and ask.

You need this question answered right now in order to meet a deadline.

If there’s a deadline looming and you need to learn how to do something fast—like, faster than fast—this might not be the moment to waste time Googling. Acknowledge that you would have rather taken the time to learn by yourself, and ask away.

You made a medium-to-large mistake.

Did you send out an email blast to 20,000 people only to discover a link was missing? Accidentally cc: a client on a thread that they definitely shouldn’t have seen? This is the right time to fess up and get advice fast. It’s probably not the first time your manager has seen this particular mistake—it’s possible they’ve even made the same one—so it’s wise to get their input as quickly as possible, even if you’re nervous.

Something unpredictable happened, and you don’t know what to do.

If someone’s making inflammatory claims about your company on social media, a coworker from another department asks you to do a large project that doesn’t seem related to your job, or your CEO drops by your desk and requests that your department change its strategy, these are all great moments to talk to your manager.

These tips may seem small, but they’ll go a long way towards making you into the kind of self-reliant worker your boss will feel comfortable trusting with more and more responsibility. There are no stupid questions—but sometimes, you’ve gotta ask yourself first.

by Richard Oneslager, 2016 Fellow

After weeks, maybe months, of writing cover letters, sending out resumes and going on interviews, finally getting an offer can feel like crossing the finish line and winning the job hunt marathon. Getting more than one offer feels even better. Knowing that more than one company is vying for you to join them can be an incredible confidence boost. After that initial feeling subsides, you may start to realize that picking between two competing offers can be extremely difficult. It can be hard to compare two similar offers; even after you make a decision you may still be left with many “what if” questions. When I first joined VFA as a Fellow, I was in a similar position. I was happy to receive offers from two companies — one in Pittsburgh and one in Baltimore—but I quickly had to decide which of these offers I’d accept and which I’d decline.

Of course, the first things to consider are the basics like salary, location, and benefits. If these things are more or less equal, the most important things to consider next are whether you’ll be challenged and fulfilled.

To make my decision, I asked myself these questions to decide which role, team and company was the right one for me. Look at are the role, people, company, and development. You’re going to be spending almost 30% of your waking hours there, and while a free paid lunch may be nice once a month. It’s important to make sure that you are enjoying the other 95% of your job more.

Is the work interesting?

No job description ever fully captures what you actually do in your role. I have had friends start jobs as analysts and ended up in sales cold calling prospective clients. I’ve know other people hired to lead projects who ended up becoming secretaries. With startups you really don’t know until you are there, but the better you can understand what your responsibilities would be and the more excited you are about the work, industry, and product the happier you will be.

This ambiguity can actually be a good thing, especially at the beginning of your career. If this is one of your first few jobs, you may not really know what you will enjoy doing until you do it. Maybe you saw yourself as a marketer, but are given a sales opportunity and thrive in it. Or you could be looking for an operations role and land a business analyst position. It’s hard to know what you will or won’t like until you do it. The good news is that most people rarely finish their careers in the exact role or industry they started out in.

Do you like the team and its culture?

This may seem obvious, but it can not be overstated. People really do make the difference. Being talkative and extroverted in a quiet office can be just as difficult as being the only 20 something in an office of 40 year old parents. Having a great manager, strong team culture, and working with people you enjoy and get along well with can make a job truly incredible.

If you didn’t meet with your future manager or anyone on your team during your interviews, reach out. Try to set up a quick call or meeting with someone on your team. This is not only a great way to evaluate the team and culture, but also a great way to gauge their excitement about you as a potential new hire. Ask yourself if you mesh well with them and if you can see yourself learning from them. You will end up spending more time with your coworkers than with your partner, friends or family, so make sure that these are the kind of people you want to be around.

One word of caution — be wary about joining a company for one specific person or manager. Make sure that you’re equally excited about the rest of the team and the role itself. If things change (as they often do at startups) and that person left, would you still want to work there?

How is the company doing?

If you’re positive on both the role and the team, make sure to evaluate the company itself. This includes everything from their leadership, their product, and their overall financial health. The thing that differentiates a good company from a great company is strong leadership that charts a path forward. Does the founder, CEO or leadership team have a clear vision for the company’s future?

Now, ask yourself if you’re excited about where this company is going or what problem they’re trying to solve. Ask yourself “is this a product or service that I would use?” or “is it solving an actual problem that I believe in?” You may love the culture, but if the product doesn’t excite you then it’s going to be hard to stay motivated on the mission. As much as you may enjoy the convenience of cloud storage, if you don’t personally believe in it, you may find it hard to stay motivated to get out of bed each morning.

Lastly, get clear on the financial health of a company. Ask or find out if they are profitable or cash positive. When was their last fundraise or round of investment? It may feel intrusive to ask some of these questions, but it’s not — a company that is interested in you and financially sound shouldn’t hesitate to offer some insights.

Will I grow and develop as a professional here?

The first few years out of college will offer some of the best learning experiences of your career. It’s an amazing time to learn new skills and really stretch your professional muscles to tackle unexpected challenges. Make sure that the company and role you accept offer ways to help you develop and grow in your career. The expectation to begin will obviously be that you’ll focus in on the role that you’ve been offered, but make sure that you’ll have the opportunity to take on more responsibility over time as you prove yourself.

Ask your soon-to-be manager how they see your role evolving and growing over the next 6 months to a year. Find out what the next position would be if you are successful in this one. Also ask how frequently or infrequently people at the company are able to move laterally or onto new teams. What you’re looking for is the right combination of a role that will be interesting and challenging to you right now and the opportunity to stretch and grow in the future.

These are just a few ways that I’ve approached comparing offers between competing companies. The most important thing is to recognize that you are in a great situation because multiple companies want you! Try not to get bogged down in the salary and benefits, and focus more on the work you will be doing. Make sure that the role is interesting, the team is a good fit, the company is solid, and the opportunity as a whole provides you the chance to learn and grow.

By Amy Nelson, CEO

Nine months ago, I took over as CEO of Venture For America, a national nonprofit that is mobilizing the next generation of job-creating entrepreneurs. The previous CEO was also our Founder, Andrew Yang. His were huge shoes to fill — Andrew had been named a Presidential Ambassador for Global Entrepreneurship by the Obama Whitehouse, one of the “100 most Innovative People in Business” by Fast Company, and had written a best-selling book. I was his number two, mostly laboring in the shadows and with zero national awards to my name. It was terrifying and humbling to say the least.

While it’s too early to declare victory, Venture For America is on an upswing post transition: Our Fellowship applications increased 72% this year. Fundraising is up almost 20%. We have made major improvements to our team and our programs. I feel 1000% confident that we are resilient and poised for the future.

I’ve been asked a lot about how we did it — and had more than a few coffees where I’ve shared this story with other organizations in transition. I’m hopeful that our experience can help other organizations develop their transition playbook.

So, here’s how we did it, step by step.

Preparing for new leadership

Andrew and I had been discussing my potential future leadership of VFA since late 2015, but I never fully believed that he would move on. Even after he appointed me Managing Director of the organization in early 2016, and started slowly transitioning away from the day-to-day, I always saw him as our visionary and principal cheerleader. It took several one-on-one lunches in January 2017 for me to fully believe not only that he was serious about stepping down, but that he wanted me at the helm. 

Andrew then met individually with all our Board Members to break the news. Active internal dialogue broke out, but Andrew was very clear that he wanted me as his successor. I had more than a few lunches and calls with various Board Members throughout February, all the while keeping mum to everyone except my husband about what was happening. We put together a detailed presentation to the Board for their March 15th meeting, which made the case for my leadership, but also plotted out other options. 

That night, I joined the meeting and dutifully trotted in and out of sequestration to answer the board’s questions while they deliberated. They came to a decision on the spot, no need for further meetings: they believed I was the right person to lead VFA through the next chapter. Initiating a formal search for a successor, which was likely to conclude with the same result, risked creating uncertainty within the organization. They wanted to send a clear signal to the market that I had their full confidence.

Trust me, I’m still pinching myself here.

Communicating the transition

This was the most critical step in the process. VFA has a complex and highly dedicated group of stakeholders: our Fellows and Alumni, the startup partners who hire them, donors, and our team. Fortunately, one of our Board Members, Havas PR CEO Marian Salzman, is an expert in critical communications and she and her team dived in with a strategy that we were able to roll out swiftly and effectively.

We started with the VFA team, as they would be most affected by the news and could keep the information confidential. Andrew started by telling key team members individually once the decision was made, and then we did an announcement to the full team, including an overview of the communications plan. We later hosted a series of internal townhalls throughout the transition to keep the team up to speed and ensure radical transparency.

Donors, perhaps the most critical of our relationships, came next. We wanted all of our significant donors to know what was happening before a general announcement; so Andrew and I locked ourselves in a room for three days and had back-to-back phone conversations with more than 40 of our top supporters. Looking back on my notes from that time, their comments were a huge relief:

“This is an easy set of news to take in as a funder. It’s a logical progression. We couldn’t be more excited for you and for VFA.” 

“I’m glad you were able to grow the talent internally. I always prefer to see that type of transition in an organization…Let me know what I can do to support.”

“We would be happy to write a letter of support fully endorsing this transition that you can share with other donors.” 

Next up were Fellows and Alumni, and then broader partner and supporter community. We hosted two Town Hall style conference calls to make the announcement. More than 300 people joined them. Andrew was awesome: he shared his gratitude for all that we built at VFA, and then became my hype man. He gave me a ringing endorsement that left no room in anyone’s mind that this was anything short of the best possible outcome for VFA. I then spoke briefly about my vision for the organization, making clear that I valued continuity and had a deep commitment to our community. We had some Q&A, and did our best to ensure transparency and communicate how deeply we value the relationships we have built.

Finally, the big announcement — mass emails, personalized emails, a press release, and, thanks to Marian and Havas, some splashy press coverage. Notes of support poured in from all over. Longtime supporters reached out for lunch and coffee meetings. Things were in motion — now I just had to prepare for the big job.

Did I mention that all of this happened in the space of exactly two weeks? 

Using the transition period effectively

Once the cat was out of the bag, we had three priorities: elevating my profile, building out our leadership team, and setting a vision for my tenure.

Over the five months we had to transition, Andrew and I co-headlined more events than I can count: Fellow Selection Day, Training Camp, Alumni Reunion, Board Meetings. Most critical was our summer gala, where Andrew usually gave the “state of VFA” update. This time, he spoke briefly about his gratitude and then turned on the hype man charm. I shared my personal story with the audience, explaining why as a first generation college student from the Midwest, this work is close to my heart. In order to prepare for this big moment, I had taken on as many small speaking gigs as I possibly could in two months. (Seriously, I would show up to the opening of an envelope just to exercise the public speaking muscle.) It paid off — the torch was successfully and visibly passed.

Now, we had to fill the void that my move was making in the organization. I spent much of the month of June at the same coffee shop interviewing at least a dozen candidates for our COO role. The staff must have really wondered what I was up to after folks would come in and out all afternoon. But this hire was critical. We found perhaps the world’s only child actor – turned astrophysicist – turned entrepreneur, and he has been a foundational asset to me and all of VFA.

Finally, the vision: we had engaged a wonderful nonprofit consulting firm, Community Resource Exchange in January for a full-blown strategic planning process. While it might have seemed crazy to engage in this very rigorous process amidst so much change, it turned out to be completely fortuitous. While it was by no means easy doing all the stakeholder analysis and building consensus on our committee, we were able to make our Strategic Plan public on my first official day as CEO. We blasted it out to the community and hosted virtual town halls the following week to present it and take questions (trust me there is nothing weirder than speaking to an audience of hundreds on the phone when you can’t see their faces and they are all on mute.) But speaking into the void paid off, and the positive comments regarding our new direction far outweighed the critical ones. 

Making progress

Once I was officially CEO, I set off on a tour of all the cities where we worked and a few others where we raised money. I’ve traveled every single week over the last nine months, but the facetime I have had with our community has been invaluable. Seeing the impact our Fellows are having on the ground gives me fuel to keep going, and showing up consistently telegraphs to the cities how serious VFA is about our partnerships there.

The main job of a nonprofit CEO is fundraising. This is a day-in, day-out activity that can be mentally and spiritually exhausting, no matter how much you believe in the mission. In the early days, Andrew performed pure alchemy: raising millions of dollars on little more than a vision and a promise. In the seven years since, we’ve built an incredible development team to keep the fundraising machine churning. But even with a phenomenal team, donors want to engage with the principal. We have seen results because, frankly, I’ve had something to prove. I’ve asked longtime supporters to increase their commitments — and they’ve said yes. I’ve recruited new Board Members with incredible resumes. And, perhaps most exciting, I put out a reverse-RFP to funders for bids to bring our Training Camp to a new city. We got multiple competing offers and ultimately raised $1 million in new money to relocate the program to Detroit.

One last thing that I’m proud of — we not only had a surge in applications this fall/winter, but we had record numbers of women apply to VFA. While I’m not doing the hard work of on campus recruiting, I’ve been a vocal advocate for women in entrepreneurship, and I believe that the example of my leadership made our Fellowship even more appealing to many young women. I’m excited to welcome our first ever majority-female class to VFA next month!

Still learning

There is still so much left to do. We have ambitious goals and a lot of work ahead of us. But in retrospect, there are a few things that I think helped us make it through the transition.

1. Leaning on experts – I mentioned the tremendous efforts of Havas and Community Resource Exchange above, but throughout the process the Board leaned on publications, attorneys, and experienced folks on other Boards for advice. This was critical — you can’t go it alone.
2. The “Hype Man” — Andrew constantly reinforced his confidence in me — both publicly and in private. The week after the Board’s decision, we had a critical, very sensitive decision to make, and he and I did not agree on the right call. He told me unambiguously that it was mine to make, and then stood behind me with the board to get it done. I’ve heard time and time again of Founder’s not being able to let go, but while it was not easy for Andrew, he gave me full ownership and permission, no meddling, and I am hugely grateful for it.
3. Growing from the inside — Not every organization will have the right internal candidate, but for us, building up the bench has been critical to our success. I’m continuing to elevate leaders who I think have what it takes — just like Andrew did for me.