Tag Archives: startup

Do they teach this in business school? I wouldn’t know. I’ve learned it all from startups.

Everyone who joins a startup, in the back of their mind, in that tiny little crevasse all the way tucked behind all the cortices and lobes, dreams of their bank account flooded with cash after an acquisition or IPO (and, of course, many years of hard work.)

But we all know most startups fail. Starting a company is hard work. Creating sustainable growth is nearly impossible. A lot of it is market timing. You can have a great product and fail. You can have a shitty product and get pretty far. There are so many variables no matter what company you join, no matter what stage, it’s a risk, and far from a surefire path to riches. If you want to fill your coffers there are more efficient and less risky ways.

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The Challenge of Startup Life

Never let your day job become your life. Once upon a time I heard that advice and it stuck with me. Not because it was particularly unique, but it was particularly accurate in regards to exactly what I do when it comes to jobs and my life. Working for a startup to some extent requires you to dedicate many hours of the week to your day job, which very quickly becomes your night job as well.

Startups can be extremely fun and rewarding. I’ve worked for a few of them to date now. Some stayed small with no serious momentum at any point from start to the inevitable layoffs once funding runs out. Some have grown extremely fast only to teeter on the brink of crash and burning. I’ve never seen a real success yet. But I’ve been close and the closer you get the more your dreams of the big win plague the back of your mind while you’re trying to focus on getting an impossible amount of work done. No matter how great things are going, people get burnt out. Naturally, some days are less great than others, and those days are the hardest.

Working for a startup is more like having a work family than most any other job. That family needs to remain somewhat functional over the course of a many year period, bringing in new members that fit its DNA while expanding it genetic footprint. And everyday that family mades decisions together, or processes the output of those decisions, which determine the fate of the business. Every move matters in a highly competitive, fast-changing marketplace. It’s exciting. It’s exhilarating. It’s exhausting.  Continue reading

Cha Cha Cha Changes

It’s incredible how while you’re becoming a more mature person you don’t realize it, but then you look back at yourself even a year before and you think — “wow, I’m so much more wise and put together than that woman on her best of days.” This feeling, despite making be blush for who I was (and specifically things I said or did then) gives me faith that I’ve got plenty of growth left in me, and one of these days I’ll be at a level of maturity required to succeed as a professional executive and even a mother.

It is very challenging to be an early employee in a fast-growing company. The culture shifts even faster than you are able to due to your own natural evolution. Suddenly, a role you were killing it at just a year ago is running away from you, and expectations are so high you’re not sure you can keep up, but you’ll huff and puff to prove you can if it’s possible. It’s scary and exhilarating all at the same time. It must feel similar to watching your child grow up, only if you were a cat, and your baby went from infant to adolescent with raging hormones in under a year and you’re constantly throwing a slumber party for her and her friends.

Although I’m not one to play the “because I’m a woman card” in real life (despite writing about it a lot), I have to admit that the recent realization that as our company grows, I am still only one of three women who hold director-or-above titles in our company makes me feel like I have a grander mission than helping us hit our sales goals, waiting for my stock to vest, and hoping to be appreciated by my fellow team members for my personal and team contributions. It’s all the more challenging as more senior leadership gets brought on when they are almost exclusively testosterone-driven males. No matter how hard I try, I’m still more on the all lets hold hands and sing Kumbaya and get terribly uncomfortable with the kind of in-your-face competition that permeates the business world, especially the world of startups. Not that it’s a bad thing — it is what helps a company become successful and keep fighting day in and day out when times are tough — but there is a level of that competition that starts to make people turn on each other. I’m no good at office politics — which is why I like the startup world to begin with — yet it’s time to start playing the game. And I need to be very very careful in maintaining proper alliances or I’ll be booted off the island.

Even though I’m highly critical of myself, I try and tend to see the best in other people. I realize some hold different world views. No matter, I’m more aware than ever that I’m just a small piece in this giant machine we’re building, and my piece can be replaced more easily today than it could have been 12 months ago. For some, this would like a fuel to their fire, but I tend to get more anxious the more itemized and compartmentalized my role becomes. I’m learning how to deal and to adapt, but I feel as if I’m falling further and further behind, and I’m running a race that my body was not built to win.

That said, the opportunities are plentiful and the excitement is well intact. The next few years are going to extremely challenging, and are going to push me to new heights and lows. I’m lucky that I’m finally starting to make some friends within the organization to share this ride with. It’s been lonely so far — not quite an executive, but higher than a junior-level employee —  and now there are more people at my supposed level who I can connect with. It was wonderful to spend time with these people, even though I feel like such an outsider regardless of situation, and to just be able to laugh at the craziness, and appreciate each other for our place in all of it.

My $20,000 Bet: The Biggest Risk I’ll Ever Take

Given that my largest one-time purchase ever has been on my $7,000 car, it was difficult for me to write a check today for $15,000 to “early exercise” the majority of my mostly pre-vested stock options. Perhaps I should have sought out more advice before doing this, but I feel like my life has a way of working out and this was a smart risk to make.

Worst case scenerio — I find out that over the long run, this risk has cost me $15,000 plus whatever interest I would have made investing that money elsewhere. Best case, I could become a millionaire, or even a billionaire. Most likely outcome is somewhere closer to the first option, but why not take the risk now when I’m young and can handle the set back.

The whole equity situation at startups is so tricky. You really can only get the best value out of your options if you’re able to exercise early, at the strike price, before the stock value is raised in a later funding round. But early is also when it’s not very clear how the company will do over the long run. It’s exactly like buying a lottery ticket, except maybe you know that the winning lottery ticket was sold within one specific town. You have some insider information that within this “town” someone is going to win big. Everyone else, still, is going to lose. But if you were able to pinpoint the town, or even the exact street the store is on, would you buy a ticket?

That’s what I’ve done. I wrote out my check, stared at it for a few minutes before handing it off to my boss to exercise most of my stock options. I believe that of all the companies I may work for in my life and have in this past, this is the one to bet on. The team is great, the product, while early, is solid and something that companies are willing to buy and spend quite a bit of money on. I’ve been involved in many aspects of the business, enough to know the market and believe we have a shot at really building something special.

My last startup — where I never bought the stock — never had a business model. There, it seemed silly to buy the stock. And even they managed to get acquired for a small sum. No one besides the founders got rich off of it, but at least anyone who exercised their options got their money back plus a little pocket change.

Still, as I drive around in my busted car with no air conditioning, I can’t help but think… should I have taken that $15k and spent it on a nicer car vs. exercising my stock options that a few years from now could very well be worth nothing. I guess I’ll just have to wait and see. My dream is to have a million dollars by the time I’m 30, and given I’m half way to 28, this is really the only possible way.

Should I Exercise My Right to Stock Option Exercising

Working in startups, your pay is always split somehow between salary and “stock options.” If you don’t know what that means — basically an option gives you the option to purchase a share of stock at a low “strike price” of the company. If the company does well, the price of the stock goes up, and if it does really well the nitty gritty details that can make the purchasing of the said stock through the option become less painful to think about. Trouble is, most companies, even good companies, aren’t Facebook or even LinkedIn. So exercising options early could mean to big losses down the line.

There are some tax reasons to exercise options early. From my understanding, if you have ISOs (which I do), you can buy the stock options up front, before they’re vested, and wait a year to sell them at capital gains tax rates. That is, if in a year, or after a year, they’re worth more than they were when you bought them. And that only really makes sense if your company goes public — the odds of a startup going public are very, very small. More likely, even if your successful,  you get acquired. And as I experienced at my last startup — an acquisition, even when the founders do well, might not result in a great turnout for the rest of the employees.

So most of my instincts are telling me it would be silly to exercise the options now. Why not wait? Well, my company is likely raising additional funding soon, which means the value of the option will go up. While I’ll still be able to buy the option for the lower strike price, I’ll have to pay tax on the difference between the strike price and the value when I buy the option, which could be quite a lot, especially given that I’d be PAYING for the option and owe money on it. And there’s still a decent chance that eventually it will be worth $0.

Now, I could exercise a portion of my options – take a little risk, and wait on the rest – but it’s not clear this makes sense either. There is a whole issue with AMT that I don’t understand (anyone want to explain this to me?) that you can avoid if you exercise early, so says the Internets. I’m not sure at what point you hit the AMT issue in terms of your yearly gross income.

Besides all of that, the reality is that I don’t really have the $20k I’d need to purchase all of my stock options right now. Well, I do have it — I have $130k in random investment accounts — but I don’t know if it makes sense to pull my funds from any of them to exercise my options. It’s a huge risk. It might be better from a tax perspective if, in a year or a few years we get acquired, but who knows if that will happen. I do believe in this company (which is rare) so that says a lot. Still, I’m relatively risk-adverse when it comes to money. Hmm. What do you think I should do?

Faking Passion vs. Finding Passion

It’s 1pm on Wednesday, I’m wide awake, full from a nice lunch with co-workers, and my brain is stuck at writer’s block. While I’ll never pose that I’m the most talented writer in the universe, if I have passion for the topic I’m writing about, I can at least revel in getting a lot of copy out. Without that passion, I stare at my screen for hours on end, and don’t know what to say.

Everyone has that thing that drives them, that defines their passion. Mine has always been honesty. I love telling stories, but I love telling true stories. Marketing is not exactly about lying, but your job revolves around how good you are at making tiny successes seem like major accomplishments, and to find an interesting and relevant story around the day-to-day business in order to generate excitement, leads and ultimately sales.

If there’s anything I learned from being a theatre major, it’s how to put myself into another character’s mind, to improvise, to always accept what’s thrown your way and go with it — yet when it comes to marketing writing, I always find myself a wall. I guess when I’m not personally excited about something, I fail at faking it. I’d always rather be involved in improving things than promoting things that are good, but have room for growth and fixes.

The problem is that I have an amazing opportunity for a long and profitable career in marketing, and I don’t even need to go to grad school or get an MBA to accomplish this. I don’t want to toot my own horn, but I’ve been lucky enough to fall into one opportunity after the next that has generated a solid resume (finally.) I certainly won’t be offered every job I apply to — far from it — but I’ve moved beyond “entry level” and now have 5+ years of experience with some impressive companies, and a lot of (true) stories to tell about those experiences.

Even though I won’t be CMO overnight I know if I could just get myself excited about this career path, I have a shot at really making a name for myself in this business. But I’m not sure this is the path I want to take for the rest of my life. My heart is in product, in building something people use, iterating, creating, and honesty. Marketing covers some of that, but not in the way I see myself looking back and feeling like I’ve used my true passion the right way over the years… if there is a right way.

If money had nothing to do with it, would I be on this marketing trajectory? I’m not so sure. Would I be happier in design or something related to that? Probably, but who knows. In the end it’s a job, and regardless of what your job is, sometimes it’s hard to be passionate about what you’re doing to make a living. And sometimes its better to keep your passion separate from your career, so you don’t kill it.

What do you think?

The Joys of Working for a Startup

There are plenty plusses and minuses that come with working for a startup. The biggest plus, in my opinion, is knowing when your money will run out. This gives you ample time to prepare for what’s next if needed. While layoffs still hit smaller startups, it’s not like at a big company where one day you have a great job and the next day you’re in the unemployment line. With the risk of being in a startup, you get a little more security in the short term.

I’ve never worked for a big “stable” company. One day I’d like to, even though I’m fairly sure I won’t be able to stand big corporate politics. Even though my job isn’t perfect, I love that I sit in the same room as the CEO and that for the most part, there are no secrets about the business. Not everything is out in the open, but I can ask questions and get answers to most of my questions, and I try not to pry beyond my welcome.

The cons are largely in not being in charge and having little control over the direction the startup will take. If you are in control and you have VC backing, that’s a lot of pressure on you. I’m not sure I could take that kind of pressure, so a part of me is glad that I get to sit on the sidelines and watch the game plays, even if I don’t always agree with them.

Still, it’s tough to know the date your job may end. I’m lucky that I’m young and single with an emergency savings account so being unemployed for a little while won’t kill me. The question is, though, when is the appropriate time to jump ship? Do you wait and go down with the ship, and receive the honor that comes with that, or do you wage a full on job search?

So far I’ve sent out a few applications here and there, but the economy is limiting options and I haven’t even landed an interview yet. My whole life I’ve been a roll-with-the-punches type gal, and I’ll probably ride this little adventure out the same way. After all, my professional life has been a series of ups and downs leading from one job to the next, bringing me closer to whatever my dream job might be. When I got laid off from my part time admin job one morning and three hours later got a call from the company that would, within a week, offer me my first full-time job I knew to just trust the way the world works. I don’t believe in God or karma, but I think things work out in the long run. In the meanwhile, you have to be smart, especially when it comes to finances. I’m no Einstein of dough, but having all my savings makes me a lot less nervous about the day, likely in the next year, when I will be out of a job.

Economy Woes

Some people, some people who have a family to support, have lost their jobs. By those standards, I’m doing fine. I’m doing great! But it still sucks to see business opportunities, especially fairly stable ones, in the middle of the fiscal crossfire.

For the last two years or so, I’ve been providing copy to my uncle’s one-man marketing firm. It started out as a gig writing some article summaries, and I made $50 a month. Over time, we upped it to more writing assignments and a $400 retainer. That was when times were good. Now, some companies are cutting back on their e-marketing budgets, which means they’re cutting back on him. And he has to cut back on me.

The good news is that I still have my day job. Well, it’s a day job on a contract that expires Jan 22. And my company is also, howdoyousay, skimming the fat from the company. Contractors are the first to go. We still have a good runway of VC bucks behind us, but they’re now concerned that even with that, we won’t make the revenue we need through advertising and other means because the economy is vacationing in the gutter. I’ve only been working there a year and a month, but in that year the world has changed. I may not have a job come Jan 22, and that’s freaking me out.

Chances are, if I do my job well – and i need to do my job well – they’ll keep me on as a contractor. I’ve been pushing for a full-time gig (which basically means I’ll get some employee-pays-a-little health benefits and won’t have to pay self-employement tax) but they’re pushing back, saying that they need to be really careful about new hires. Of course, I’m supposed to work from the office 4 days a week and 40 hours a week, which seems legally to be an “employee.” But what do I know?

I recently took advantage of my contractor status by traveling and working remotely for about 2.5 weeks. It’s a double-edged sword, because they could very easily use that against me when deciding whether or not to hire me full time. I probably should be in 5 days a week if I really want to get hired on. I guess when it comes down to it, I’m not sure I’m thrilled with the idea of trading in my one-day-a-week work-from-home gig for health benefits. Sounds stupid, but with my anxiety disorder I need a day to just be away from people and focus on my work.

So… my uncle hasn’t gotten back to me on how much I’ll be making a month now that one company cut their monthly newsletter to quarterly. But it won’t be $400. That $400 really put me in a comfortable salary point given my cost of living. Plus, if I ever want to actually save up for year one of grad school before I go, then I need the money. That doesn’t seem possible either, though.

10 Reasons Why I Love My Freelance Job

I work for a web startup in Silicon Valley on contract, about 40 hours per week.

10 Reasons I love My Job:

1) The people I work with are passionate, fun, and great collaborators working together to create something new.

2) My job tasks are diversified and include many things I’m interested in, such as writing, community management, UI, and QA.

3) The room to grow at my company is only limited by my skills and interests.

4) I get paid a very decent monthly wage for the opportunity to do something I love.

5) Because I’m on contract, I get the flexibility I need to pursue my other passion: theater directing in the evenings and on weekends. I’ve applied for numerous web startups, but most wanted me full time at 60+ hours a week. If I had no life outside of my job, I’d be happy to take this on. However, I need to have balance in my life. I don’t mind sacrificing company-sponsored benefit plans, sick days, holidays and stock options if it means I can keep doing what I love AND have a job I love.

6) While I don’t have a lot of time to do “other freelance projects,” I have a few hours a week that I can move around to take on some extra work. I like to continue freelancing on additional projects because it’s always good to have side income in case your full-time (or in my case, 40 hour per week freelance) gig goes kaput.

7) Free lunch on Mondays!

8) I feel appreciated. My ideas are not always used, but at least they’re considered. People seem to respect me. That’s the most important thing in making me feel satisfied at a job.

9) Flexible schedule and work location. I work from the office 2-3 days per week and I work from home the rest of the time. I find I actually do more work when I’m at home because I can focus. I’m also not anxious like I was at former jobs where I just didn’t feel smart/competent/knowledgeable enough to feel comfortable yet still challenged in the position(s).

10) My job is a great stepping stone to whatever comes next. I’m learning so much, and I learn more every day. As a writer, I’m still involved in research and finding out new things. As a community manager, I get to do my favorite thing ever – help people. Is it so absolutely bizarre that I actually love responding to customer feedback and writing FAQs? Being involved in QA, I’m learning a lot about testing a site for bugs. In general as a marketing assistant and such, I’m learning a bit about product management and general marketing for a web startup. I think all of this puts me in a great spot to move on to bigger and better things later in life, whether that be a position with more responsibility at my current company or something else. A while back I applied to a community manager position at another startup and it came down to me and someone else. I didn’t get the gig, probably because my journalism experience wouldn’t directly cross over to interacting with site users on a daily basis. But now… my resume can potentially land me another community management job, if I ever need to look for another one down the line.