‘Cause I wanted to. THE END!!

Okay, okay, just kidding. The change may seem abrupt to those who don’t know me personally. For those that haven’t religiously followed my journey, first of all, fuck you!!!

Give. Me. Attention. Photo by Styled Portland.

What about all this [points to self dramatically] makes you think that I don’t need your constant love and affection?

To understand the big change, here’s a sequence of events that you might find helpful.

I began my career working in investment management in San Francisco. There, I was working as an Investment Counselor, working directly with high-net-worth clients. I answered questions about the markets, kept them apprised of portfolio strategy, talked to them about football (much better than talking about the debt ceiling) and pretended to care about their problems. (I didn’t.) Basically, I LET OLD RICH WHITE GUYS BITCH TO ME ABOUT THEIR MONEY ALL DAY.

Helping rich men get richer? Yeah, that shit had the shelf-life of whole milk in the hot sun.

So, I got scrappy, saved up all my money—hence the nickname, Dumpster Doggy—quit the job I hated, and left to travel for a year. When I left, I thought I’d leave the money space altogether, but ultimately decided that maybe my work *here* wasn’t done. I came back to my hometown of Portland, Oregon, to work on writing a book on investing, for young women.

What I thought would just be a landing pad for a year or two turned into a four-year stint. Funny how that happens. To summarize my time in Rip City, I worked on the book, realized how fucked it is to get a traditional book deal when you don’t have two-million Twitter followers (I didn’t really use social media at the time), tabled it (temporarily?), and ultimately turned around and created a business. First, I started the speaking and doing investing seminars under the name Invested Development, which remains the name of my business. Next came the blog, then social media. (So basically, I did it all backward.) Admittedly, it took me a while to feel comfortable with my income sources, which are 1) freelance writing 2) corporate speaking and events 3) my online course, and occasionally, 4) one-on-one coaching.

When I’m being a giant asshole to myself, which happens more than I’d like to admit, I bum out over how long it took to get to where I am now. But then I get ahold of my damn self and have a little perspective: if you had told me four years ago that I’d soon have an all-new career as a Real Working Writer and business-owner in NYC, I think I’d be pretty dang proud.

I never thought I’d live in ol’ Stumptown forever. I love Portland and it will always be my home, but I’ve always struggled to square what I consider to be its darkest demerit: sweeping homogeneity, in every sense. This city has been so good to me in so many ways, like a safe boyfriend, but one who always wants to stay at home to watch reruns of The Office. Which is great!! But sometimes you gots ta kick the perfectly-good-but-boring boyfriend to the curb and find yourself a wild f*ckin animal.

The hardest part of leaving Portland isn’t the cheap rent (I paid $650 and lived in a house with a backyard, a cat, and endless storage space for my fake beards and nipple tassels), or the easy access to zee great outdoors, which has been crucial to my sanity as I started over in my career, or even the fact that you don’t have to trade your god damn first-born son for a cocktail at a bar. (For anyone that is curious, $17 seems to be the going rate for a tiny cup of delicious, delicious poison here in NYC.)

Favorite campsite in the Pacific Northwest.

The hardest part, without question, is leaving my family and friends. I cherish the time I got to spend with my mom, dad, and brother, whom I haven’t lived near since I was 18 and left for college. I finally feel like I was hitting a stride and making friends that actually wanted to hang out with me. But you know what they say about having people that love you!!? Drop they asses so you can be the loneliest girl in the most densely populated (and rat-infested) city on the complete other side of the country!!!!!!!!!!!!!!!!!!!!

New York City scares me, but maybe not how you’d think. Mostly, I’m concerned about the type of warfare my sweaty-ass face will take on my adorably coifed bangs. I like my bangs, but I’ve a hunch that the NYC summer, with its heat so thick you can eat it, will feel differently. If you need a visual as to my natural hair texture, here are a few of the absolute hair legends that I’ve been compared to in the past: John C. Reilly, Richard Simmons, and actually, just those two. They are the only ones.

I’m the one in the middle.

I’m only kind of kidding.

I am also worried that I’ll feel lost here and that I won’t be able to “cut it” and that New Yorkers will take themselves too seriously. The city that never sleeps?! Ugh! That sounds exhausting and white drugs are expensive! I’m too old for that shit. But two weeks in, this hasn’t been my experience. And if anything, maybe I can be the one to help loosen up this joint with my relentless self-deprecation and refusal to wear anything but Birkenstocks. Although I hear that’s a bad choice on the subway, and that I’ll need a closed-toe option. Strongly considering tie-dyed Crocs, but am open to suggestion in the comments.

In addition to just wanting to be here, there are certainly business reasons for me to live here. At some point, I should probably make some attempt to “be in the media.” I don’t know how, but there’s that. More importantly, my business is to educate women to the point where I can kick them out of the nest like the proud but ruthless mama bird that I am. You ain’t pay rent here!! Many will note that this is an atrocious business model, but imma stick with it. And for this, I need a revolving door of women who are ready to learn. In New York City, I have access to the maximum number of badass babes. This is also good for me, personally. I desperately want to be around women who are my age who are doing cool shit, for synergy and whatnot.

While I think this makes sense business-wise, I wouldn’t have moved for only that. I am here because I want to be here, which I think is a pretty damn good reason to do something. So, you can find me during this inaugural New York summer washing the black, radioactive slime off of my lower legs every night when I get home to my cockroach den in deep Brooklyn. It’s gonna be wonderful.

Aside from the cockroach in my bathroom, my first friend in NYC.

So, here I am! Now, I know what you’re thinking: I want to help this lonely woman. (I am not actually lonely. Just shaking every person’s hand I see on the subway. That’s normal, right?) Here’s how you can help me (which will also help you!!):

Do you want to be my friend? GREAT! Take me out for a bite to eat or a drink at your favorite spot. You should emotionally prepare for a person who is simultaneously SO FUN at parties and SO NOT FUN at parties. (Think: a tray of Jell-O shots and good music blasting followed by a treatise on why men need to step the fuck up for women’s reproductive rights.)

Do you want to date me? COOL BEANS!! So long as you’re interested in the type of woman who waits too long to try to find a restroom until it becomes an emergency almost every single day, we’ll make a great match. Yes, I am 34 years old. Which also means that this ol’ pre-corpse has already begun its slow march towards death, but please believe that dating an old lady comes with its benefits: I’m past the age where I need any of that fairytale shit. Let’s just have some motherfucking fun.

Do you want to hire me? EVEN BETTER!! We have options:

1.) Getchur employer to bring me in for a corporate Invested Development (Investing 101) seminar where I teach ya all about those retirement plan options (and beyond). You gots the damn thing; now it’s time to understand how to use it. I make these seminars fun as hell so don’t worry, you won’t wanna spoon your eyeballs out like you do when Fidelity Frank or the 401k Fred does a company benefits prezzie. One attendee even called Invested Development “Suze Orman meets Broad City!” <3

To put the wheels in motion, figure out if you’ve got something like a women’s leadership or inclusion group at your company. That’s usually who I work with, though I’ve also worked with HR departments, internal events, and culture departments. Honestly, I think corporate workshops are fuckin’ genius (if I do say so myself) because then you get YOUR FACELESS, FLUSH-WITH-MONEY EMPLOYER to pay for all this sweet, sweet education. And yes, I travel (and love to travel)!!

Email me at AmandaHoldenInvesting@gmail.com for more information!

2.) Similarly, round up your friends for a Wine/Tacos/Hot Tea/Knitting + Invested Development night. Whether it’s a ladyclub you’re involved with or just the island of misfit toys you call your friend group, this is a venue in which I really shine. I love an intimate educational night, who’s with me?? Again, shoot me an email or send me a message on social meeds. 

3.) TAKE my online Invested Development course, SPONSOR a woman to take my Invested Development course, or SHARE this service with the women in your life!!

What I am PROUD and CERTAIN OF is the value and benefit of this course. I’m not aware of anything else in the whole-wide-world like it. But what I SUCK AT is the whole marketing thing. I shouldn’t admit this as a business owner blah blah IDGAF, I have no background in sales!! My background is in—get this—investing!! So, it sure would warm this old harpy’s heart if you’d share it with your loves so that I may continue to invest 30% of my income while blowing the rest on Taco Bell, costumes, and now, $17 cocktails.

Thank you, to everyone, for your support so far. Some of you know this, some of you don’t, but starting something on your own is really hard and confusing. I am overwhelmed when I think of the wonderful people who’ve rallied along beside me throughout.

To the next adventure!


  1. Britt @ Tiny Ambitions on May 16, 2019 at 2:25 pm

    Can I live vicariously through your awesome New York adventures? K thx. In all seriousness, I’m super pumped for you and what New York means for your business. It’s supercool that you decided to take the leap and out yourself out there. Also, your marketing strategy is dope. Every time I see you in your Insta story with a load of bread, it makes me freaking day.

    • Dumpster Doggy on June 6, 2019 at 4:07 pm

      Thank you, Britt <3

  2. Deanna on May 17, 2019 at 4:52 am

    I loved reading more of your story! You’ve got a good thing going so keep on keepin’ on! Some people follow formulas when stating a business and it may work for them (not I). However, IMHO the passion and drive are the meat of it which leads to success. You’ve got both so I think you’ll go far. All the best to you in NYC!!

    • Dumpster Doggy on June 6, 2019 at 4:07 pm

      This is so wonderful. Thank you <3

  3. Kristie Le on May 17, 2019 at 1:48 pm

    I am so proud of you!! Keep Dumpster Dog alive and keep us updated on your adventures! I have a really good Irish friend in NYC, you guys would totally be pals! Find him bartending and doing standup at the Grizzly Pear when you’re not too busy being a badass boss lady 😀 Love you!! <3333

    • Dumpster Doggy on June 6, 2019 at 4:06 pm

      I love this, and you!!

  4. Annie on May 20, 2019 at 3:01 pm

    Hi! Welcome to the east coast! I live in the part of New Jersey where people from Brooklyn move when they have kids. Except I don’t have kids, but I still like it. Anyway, I’m around and we can find happy hour deals whenever you think you want to hang with a 40year old from jersey.. And you can totally wear open toed shoes on the subway, as long as you have a good pedicure, no one wants to see that.

    • Dumpster Doggy on June 6, 2019 at 4:06 pm

      Lol if by pedicure you mean I occasionally remember to cut my toenails, we good. Let me know next time you’re in BK!

  5. Sarah on May 31, 2019 at 1:10 pm

    Congrats on your move!! You’re going to do awesome! Because that’s who you are girl! Hopefully I’ll get to see you when I get up there next! Till then meet some girls and make some $$$$

  6. Nichole on June 12, 2019 at 12:49 pm

    I love this! Wow.. I just stumbled upon you in the Dream Warriors Opportunity page and I LOVE your story! It couldn’t have come at a better time, and I too am wanting to drop it all and move to New York! I, on the other hand, am trying to find a gig up there. Event if I don’t I may just go move anyway! YOLO! I currently work in Marketing and Events for a staffing agency (blah..not as sexy as it sounds.) But if..(scratch that)..WHEN I move to New York I would love to be friends in real life. 🙂 And if you know of any gigs up there, let me know! I love Atlanta, but ready for a drastic change!