227: "Super Extrovert" Pivot Strategies with Photographer Phillip Van Nostrand
8 Dec 2025 · 30 min
Photographer Phillip Van Nostrand made 143 personal calls during lockdown to stay connected, then pivoted to FaceTime shoots and socially-distanced sessions in Central Park. He booked multiple $10k weddings with 50% deposits upfront and joined community groups like Cave Day to rebuild his network.
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What's next? This is a question we're all having to ask and answer more frequently. I'm Jenny Blake, your host of the Pivot podcast and author of Pivot. The only move that matters is your next one.
For show notes from this episode, visit pivotmethod.com podcast if Change is the only constant, then let's get better at it. Here we go.
Welcome back everybody. I am so delighted to be here today with my friend Philip Van Nostrand. Phil is a photographer. But even more importantly, when Michael and I were throwing together our very agile wedding at City hall in New York City Back in November 2018, with just a few weeks notice, I asked two friends for a photographer recommendation. Two separate emails. They weren't on the same thread and in the same day, both replied with the same person, that is today's guest. Which was all the serendipity I needed to say yes. So Phil is here. He was an instant friend, exactly the kind of guy you'd want on board for big events. And I would describe him as a super extrovert. So when we connected during this pandemic. Thanks to Phil, of course, because why would I reach out to anybody? I it's as much as I could do to respond. But when he reached out and we connected, I thought I have to have him on the show to talk about the extroverted strategies that you can run and how he's earned $15,000 during this time, even with so many events being canceled, you would think that it's quite a devastating time for photographers. And yet Phil is as joyful, as happy as ever, networking up a storm. And I thought we just got to talk about this on the podcast. So Phil, welcome to the show.
Yay. I'm so excited to be here. Thanks.
I was so happy that you reached out and I couldn't believe when you were telling me your strategy that you've done so much. I would love for you to just kick us off by sharing what was going through your mind back in March when all the events started getting canceled. And then how did you shift into total action mode and even share what your calendar has looked like for these last few weeks.
I just chuckled when you said you wouldn't reach out to anybody during this time.
I'm just so bad at proactively reaching out. I kind of.
Yeah, it's so funny. I.
When things started closing down, I realized a lot of people were doing little meetups online. You know, I have a few sort of active Facebook groups that I'm a part of through different communities, like the weddings community and the entrepreneurs community and things like that. Photography friends. And I was seeing people starting to post that they were doing little zoom happy hours or a webinar on this thing, or someone was having a town hall meeting about the SBA loans. And I just started. I turned on notifications to all of these groups and then forced myself to go on Facebook daily just to see what was happening where. And then I just put them all in my calendar. And then I was, you know, starting to reach out to old friends. I had time on my hands to, like, be home and just sort of think about people that I've missed in my life and started making phone calls. So then I started. I created a list on my calendar, and I just started adding, you know, every time I think of someone, you were on the list. It was like, jenny Blake. Oh, I miss her. I just saw one of your newsletters come through. I'd love to chat with you sometime. So I threw you on my list. And then at some point in the last two months, I ended up calling you or texting you to see if you would like a call.
You said something interesting where you just place a phone call. That rare event of you actually just try calling people. And how has that worked out for you? And then what's your strategy if they don't pick up?
Yeah, I have a couple of strategies with the phone calls. Actually, I did accounted. So as of, like, two weeks ago, I had made 143 phone calls with actual friends. Like, not just attempts, but I talked to 143 people. My strategy is if I'm feeling bold, I'll just cold call them. Most people don't pick up during the middle of the week. I realize that people are a little busier with their own things that they just don't want to be interrupted. But I'll call. If they don't pick up, I won't even leave a message. I'll just text them immediately and say, hey, I was just thinking of you. I miss you. Would love to catch up if you're Interested, let me know when you're free. And then it sort of puts the. It allows them to choose a time and someone's free at some point in the next two weeks. So then I can schedule.
I like how you're just willing to put out there, hey, just want to connect. Message me anytime you're free. And then even I think you had said to me, like, in whatever format, something like phone zoom. It was so chill.
Yeah, a lot of people, I think, have zoom fatigue. And I'm very, like, sensitive to other people's space and time. And. And, you know, I don't want to, like, talk to someone for someone to talk to me on zoom if they've just been on zoom for like, eight hours that day. So, you know, even some. I just talked to a mom, a new mom the other day, and I knew that with her company, she's on zoom all the time. So I just told her, like, hey, well, we could just call and you could just walk around and do whatever you want.
So after 140 plus phone calls during these last weeks, do you have phone fatigue? Are you, like, are you feeling, oh, I'm going to need a break, or are you just getting more energized by the day?
Well, yeah, as you mentioned at the beginning of the podcast, I do feel. Feel like I'm a super extrovert. So I feel like my day has been really successful. If I've talked to two or three people and it's only like two to five people a day, that sounds like maybe a lot to some people, but for me, like, two people in a day could be like one in the morning and one in the evening, or sometimes they're just like 30 minutes. I feel really energized. I feel like I've connected with cool people. I've gotten jobs out of this. I'm, like, staying on top of people's minds. It's not just a business strategy, but it just feeds my soul, you know.
You did describe how you've earned quite a bit during this time, actually, which I find so surprising because events are one area that have been hit very hard. You're a photographer. A lot of your work does involve being in person. What do you think has led to you being able to book so much business right now, even if you're just taking deposits?
I think at the beginning of this, I just sort of, you know, back in, I would say, late March, I just figured, okay, I think I can hold my breath, you know, financially for about two months. And then if things loosen up, I'll probably start booking gigs again. I wasn't really planning or had a, didn't have a strategy around booking gigs. But I would say early April, a ton of people started reaching out to me asking me if I was free for dates later in the year or the following year, 2021. And so I actually sent out 11 proposals for mitzvahs and weddings and things like that from planners in Dale, Colorado, planners in Dallas, planners in New York. And so out of all of those I booked, I want to say four, potentially five here. You know, those are like $10,000 weddings for me and I can take a 50% deposit on them. So I actually put some decent money in the bank right now, which feels really nice. It feels like I'm working when I get to write a proposal, you know.
I know you said too that sometimes those connection phone calls would lead to you being top of mind for somebody. They say, well actually now that I have you. And even I was said, actually now that I have you, let's do a podcast. Which I, to be honest, probably would not have thought to do just cuz I had no idea what you were up to during this time.
This is my fourth podcast recording that I've been on during this time too actually.
You also host a podcast club that although I haven't been able to join yet, Phil said it was okay for me to mention because I wasn't sure if it was this private thing for only his close friends. But of course, being a super extrovert that he is, and I have to say, pivot podcast listeners are pretty amazing. I mean, if any of you want to join, he's going to give you the link to put in the show notes. But I love how you gather people around podcasts as well. Tell us a little bit about the podcast club.
This is, I have to say that my podcast club is, I would call it, my favorite hobby in my life right now. I was at a party or like a little house gathering with a friend and I was talking to someone, she was talking about her book club, we were talking about podcasts and then she was like, I wish, I wish there was a podcast club, you know, And I was like, oh my gosh, we should do a podcast club. I love, I love podcasts and exactly like a book club, we just listen to one podcast each month and then gather over drinks and discuss in real life virtually. We're, we're doing every two weeks we're listening to one podcast, usually a limited series podcast, like something that has a season.
And then we gather on Zoom for about two hours, an hour and a half, and discuss the podcast. It's great. We're listening to Ear Hustle right now, which is stories from inside and outside of San Quentin prison. It's great.
Yeah, Ear Hustle. I saw that. You did Dolly Parton, right? That was the one.
Yeah, we did Dolly Parton.
Did you also do the Dream, or was that. Because what Phil does is he emails the whole podcast club and has them vote on which series they would like to choose next. So I always see at least the narrowed down list of what you're voting on. But being the super introvert that I am, I have yet to show up. Sorry, Phil. I'm sorry. We're impossible. I really think it's a huge advantage if you actually have a super extrovert like you. It's just such an advantage because. Anyway, I. I digress. But. But I love it in theory.
You know, you could sit in the background on a Zoom call and not have to interact very much if you wanted.
Okay, see, that's already something.
Yeah.
You know, but there's no pressure.
You could do it.
I wanted to start a podcast club. My brother, dad, when my brother and his wife were living in Brooklyn, and then my dad came to visit, we were. We kept talking about all these podcasts and I do think it's so. It'd be so. There's so much fodder for discussion and it's such a great way to gather people, especially now during this time. And you, you've been doing all kinds of. You, you're part of Cave Day. Engage besties. Like, Cave Day is a really cool. Explain to listeners what Cave Day is. Cause I bet others could simulate this, although they have a really good thing going.
Yeah, they do. And it sounds like, so simple. When you hear it, you'd have to say like, why would I pay for this? But Cave Day is essentially.
Right now, it's an all online format through Zoom that helps facilitate deep work sessions. So you'd go in with a project in mind, like, I'm going to redo my website or do my taxes today, or edit this podcast or, you know, whatever, whatever. The big important project is not just emails or updating your Instagram or anything. They encourage you to put your phone in the other room, turn off notifications on a computer, no emails, no nothing. And then you just do a deep dive together, but separately on your own projects. And it's really well facilitated. And I think the group dynamic kind of helps keep people accountable and I just had a Forbes article out about them this past week, and the writer said, like, I got. I finished this article in one Cave Day session that would normally take me two weeks to write. It's that kind of. Kind of output. It's really cool.
That's so awesome. Once again, I've seen this. I've seen this offered. I think my friend, our mutual friend Monica was one of the people who recommended you. Oh, man, Phil, this is going to turn into, like, a therapy session. Don't ever leave the house. No, it's okay.
No, but lay down on a couch after this call and relax.
It did. It did look awesome. And it's cool to see how they're shifting during this time because it was meant to be. Cave Day is. And was in person, and yet the format is still very innovative, and I love the intention behind it. I got to do it, especially now that it's virtual.
Yeah, you'd like it, I think. And there's, like, minimal interaction, so you really are not my jam.
There's also a silent book club in New York. Did you know that?
Oh, yeah, I've heard of that, actually. You're all sitting together reading, right? Yeah, yeah, I've heard this. The cool thing about Cave Day is that I talked to one of the founders, and he said that they're signing on, like, 20 new members a week, I think, and it's only $35 a month for, like, unlimited sessions. They happen in the mornings and in the afternoons and. Yeah, every single Monday through Friday, some Sunday sessions to. So it's really, honestly the most I've ever gotten done in my business, in my life has happened during Cave Days. I wrote that whole Medium article that you read in Cave Day.
That's incredible. That Medium article that Phil's referring to is called how to Live an Epic Freelance Life in the time of COVID 19. I'm going to throw it into the show notes of this episode, which I believe will be episode227. So you can go to pivotmethod.com227 to get all these links. One of the things you say in the article is that you typically travel about 100 to 200 days a year. What has it been like for you as not just a super extrovert, but a super traveler being home for this long at one stretch of time?
Yeah, it's funny, you know, people ask me this a lot, actually, and I don't. I'm okay. I have to be very honest. I'm, like, very content in my Environment, wherever that environment may be. I found that like my extroverted tendencies get fulfilled by the amount of calls and connections I'm doing through the day. Which is fine by me. I'm excited to travel again. But I. I don't. I don't know how to describe it, Jenny, except that I think there was a time in my life when I didn't travel all the time. And I was really happy then. And there was a time when I like didn't eat out all the time and didn't network as much. And I was happy then and I'm still happy when I'm busy and I'm happy now when I'm not busy. So I think I'm really just content.
I would even describe you as ebullient. You are like so bubbly, so always in a good mood. We had never met, by the way. Phil and I had one phone call before Michael and I got married and we didn't have any family fly in.
The day before that you were getting married, by the way.
You were like, that's when I confirmed. No, I talked to you before that. I at least had you save the date, right?
You mentioned it. Yeah. You said maybe these days, but we're really not sure. I feel like you can do it like one or two days before. I'll have to double check.
Listen, that's what happens when you marry a rebellious non planning artist. Like I was losing my mind. I'm like, Michael, I'm not trying to be bridezilla, but we have three weeks to go. Listen, like, I don't care if we ever get married, but if it's gonna happen in three weeks, could you just let me know? Because it's not that he had hesitation, but he's very. He bought his entire outfit the day prior. The afternoo prior. And yet he looked great. He found a killer outfit. Neither of us wore formal. I wore a white jumper.
Your pantsuit was stunning, by the way. Thank you.
Thank you. I had a white jumpsuit because this is not on social media. I'm sorry, Phil, that we haven't yet shared your beautiful photos.
The family loves them. There's one sitting right at my desk right now. But I wore a white strapless jumper from Reiss. Shout out Ina who told me about Reese. I'm obsessed. And then a lace overlay. There was actually a wedding. The one weddingy thing I got, and it's my friend Anne had come over just before I was getting dressed. Hair, makeup, et cetera. And once I put the lace on Ann said in her classic Italian accent, Italian jersey. Like, now that's a bride, you know.
So, Phil, thank you for being so game that we didn't confirm with you until the day prior. That's hilarious. I kind of. It's all a blur to me now.
No, I had my calendar, so the time was available just in case.
It's also one of those scenarios where we're so different. We just did a whole series on the podcast, but our Venn diagram in terms of planning something like a wedding, it just never overlapped. Like, his process made me so uncomfortable and my process made him so uncomfortable. Even within a month span of time. I'm not even talking a year and.
A half like crazy. I know. Yeah. That's so wild.
You wonder how we can be married at all, but it works.
Somehow it works. Most couples are planning their weddings like for nine to 12 months. It's so crazy.
I'm so happy we didn't do that. I'm so happy that we didn't choose one piece of silverware, one napkin color. Like, I was so happy with how we did it. And this is a very tangential way of saying you and I barely knew each other and yet you were a fifth of our wedding, you know, maybe like a seventh of the wedding participants. And you just fit right in.
Join you for lunch? Actually.
That's right.
Remember you invited me to the brunch. So I just came and sat down and I would jump up and take some pictures, sit down and eat some food, jump up and take some more pictures. It was really lovely.
It was, it was fun. I really recommend this. I know this, this episode is not necessarily about planning an agile wedding.
But.
I mean, it's very apropos of the life and the circumstances that we're living in. I mean, you did a 10 person wedding basically, or seven person wedding. And that's pretty much going to be a big trend for the, you know, near future.
It is apropos for these times. In fact, our next Medium article we can co writes, like how to have a, you know, city hall wedding or kick ass city hall wedding that you plan in three weeks.
All right, that's your, that's your cave day task.
Okay, I'll take it.
One thing you mentioned earlier that I didn't share. You asked me how I was doing creative photo shoots during this.
Yes, tell us.
Yeah, I saw a model friend of mine post some pictures that looked amazing and the caption of her Instagram post was like FaceTime shoot with this one photographer. And so I Went to this photographer's page and all his pictures look so good. But he had done all of these shoots via FaceTime. So, like, within 24 hours, I had texted a model friend that I had worked with before and set up a FaceTime shoot. Figured out, like, how it worked, what to do. It wasn't a screenshot. I wasn't taking a picture with my cam, you know, with my camera of my phone. It was in FaceTime and I got the coolest photos. And I've done, you know, as of this recording, I think seven or eight virtual shoots this way in Montreal, in Spain, in Los Angeles, in Bushwick, Williamsburg in New York City and Virginia, actually.
Are you taking screenshots with your phone?
Well, okay, so the little secret is if you're on a FaceTime call with somebody, both of you have to have FaceTime. That means you have to have an iPhone. And then there's a little white button in the middle of the screen. When you click on the screen and it says FaceTime capture. What that button does is it takes a picture of the other person through their camera without you in it, and then it sends it to me. So if I'm having a FaceTime with you, Jenny and I hit FaceTime capture. It's just going to capture your screen of you and it'll give it to me and then I'll have a photo.
There's a great pro tip.
Yeah, it's cool. It's really fun. And the photos are like, still kind of low quality, but with the right editing, I think they look amazing. And you can see it on my personal Instagram.
Share with us what you're.
I have like, yeah, it's PhilipVn P H I L L I P V as in Victor. N as in Nancy.
I'll of course put that in the show notes. Wow, that's fun. And you did a FaceTime photo shoot several now and then. You also did a socially distant or physically distant photo shoot in Central Park. How did that go?
I did. It was a couple who, they're getting married next year, but she's pregnant now. And I think she wanted photos before, you know, she started showing her pregnancy. And also she actually wanted pictures in her wedding dress before she had the baby because she was afraid that she was going to lose her figure or whatever. And so she's this tiny Asian girl. She was definitely not going to lose her figure. But I said yes. We went to Central Park. I didn't shake hands or hug them, but. But we had an empty park at 9am on a Tuesday morning and we got the best pictures right around the fountain and the, the mall over there that's usually packed with people. So I got these really awesome photos of this like empty courtyards and tree lined avenues and it was just really beautiful. I got paid almost, you know, over a thousand bucks. It was really wonderful.
I know it's a photographer. It's a photographer's dream really, that if you're going to do a shoot like that, there's no one around. It's so rare. It's as if you have a movie production budget to wall off this area, these normally so public areas. So what's next for you? As the talk turns toward opening up, and yet no one really knows what that's going to look like. How are you, Phil, approaching this?
Okay, this is crazy to say, but I'm actually flying to Napa, California in less than two weeks. On June 1, I'm flying out there to do an engagement shoot with a couple. We had planned this like months ago and they're from out of town. They were going to do a site visit at their wedding venue in Napa. And I just messaged them like two weeks ago, hey, you guys still planning on going to San Francisco on the second? And they said yes. So this last week I bought my plane ticket and I'll be heading to California to do my very first trip in about two and a half months. And also my first big shoot out in California, which is going to be cool.
How do you feel about braving the airport and the airplanes and all that?
I feel good. I'm definitely not like a worry type of personality. I'm a little bit more on the high risk, like I like to play poker kind of personality. But I do have like a KN95 mask. There's. There was a. Actually a vending machine that opened up in my neighborhood that was selling the Chinese version of the N95 masks for $4 a piece. So I got them. I'm gonna wear it the entire plane ride. The plane wouldn't allow me to book middle seats. So there's all these gaps between people. And there's also. I picked the front row, the front most seat that I could. And there's like nine, nine empty rows in front of me. So it's a very, very empty plane from what I can tell right now. Yeah, I'm gonna arrive. I think I'm gonna take a test. I guess there's like lots of free tests that you can take in California right now. So I'm gonna land and Try to take a test within a day just to see if I have anything and I should be good to go.
That's so. That's so interesting that California has more. I mean, I guess it makes sense, more tests available and that you can take it when you arrive. Just to know, just in case something at the airport.
But my sister in Santa Barbara was saying that there's like three different sites that you can take tests and get results within a day or two.
Right. But I love your idea to just do it at the early part of the trip and just in case you're a carrier without knowing it, which they say can happen for a week to two weeks. That's what's been so challenging, is that just when you think you're safe, well, you might have it actually and be a carrier and it's hard to know.
Well, now in New York, every single citymd site has free antibody testing, I believe. So it's definitely more available now than it was two weeks ago, I think.
Speaking of weddings, Michael and I attended our first wedding via Zoom today. And yeah, it was interesting. I would recommend if any of you out there are going to do this, appoint a younger family member, some a teenager or college grad. Find a gen zer in your life to be the co owner of the event. Because some people were not on mute. You could hear them ordering drinks at the bar or things like this.
Yeah.
So you really. It's so important to have someone that's not in the wedding or part of the wedding party actually managing Zoom. And I noticed that the photographers did have masks on, so it was interesting to see that it was kind of. I actually had an emotional moment because here you are, you're watching a wedding and the vows and that was very powerful. And meanwhile seeing photographers with the masks. So you. Although the masks may not be in the photos, they're on the photographers. So it's this kind of surreal scene.
Slice of reality for you. Yeah, I know in the events world there are some. I would do this actually. I love Zoom and I zoom and I feel I've mastered it. But there are organizations that actually offer Zoom, I would say like facilitation services basically. And they can sort of host your party so you don't have to think about it.
That is a creative. Of course there's going to be. Did this exist pre pandemic or is this a pandemic invention?
No, no.
Oh my gosh.
Like. Like they're wedding planners or wedding coordinators and they're just like, of course I Can I can coordinate something online as well. You know, a little tech savvy.
That's exactly the kind of job that one could never, ever, ever predict. Oh my gosh. I'm a Zoom coordinator for events. And yet, of course, it makes sense when you hear it. It's like somebody getting married would need to have that so the family doesn't.
Have to do it and you, you want. I think Zoom really can be either like a super interesting. If you've ever done a Cave Day, you'll see like how they, how they make it fun and interesting. You can do breakout groups in Zoom. There's like a drawing board that everybody can draw on together. There's polls that you can pop up and have people like anonymously vote on stuff. So Zoom can be fun or it can be like excruciating. And I think in the right hands, it's a good experience.
Phil, as we wrap up, I know you're also working on a book about living an epic freelance life. So. So if you could leave listeners with one piece of homework, one thing that they will do when they're done listening to this episode, what would it be?
Oh gosh, put me on the spot. Okay. How to lead an epic freelance life. I would say one thing that would enhance your life as a freelancer would be, I'll mention Cave Day or something like that. Like six degrees. Society is another thing. I found really beautiful communities or my podcast club. Find a little community to join that involves people who are like minded, like you, and join them and be a part of something bigger than yourself and find how your world expands when you join something like that. Even if it's Cave Day, which is just sort of, you know, working separately. I've met people and ended up photographing like podcast editors and have like, yeah, just had met really wonderful and cool, interesting individuals. And that is, is something that I can do only because I work for myself and I have free time in the afternoon in the middle of the week. And it's a great way to work on your business as well.
I love, I love that you shared that. Even as curmudgeonly as I can be about group anything, I have to say that for me too, some of the highlights of this time have been the very small front or groups that have popped up. And of course Zoom calls with my family, connecting with you. There are so many. I just love that advice to find. No matter whether you're a super extrovert like Bill or uber introvert like me, you just find one group. Because I Think if you resonate and you admire and respect the people in it, and then the content or the format is soothing to you, is like soul nourishing like you described it, Phil, then it is energizing. That is the kind of thing that is so enriching. And that for me, boosts me during what can sometimes be an up and down week.
Yeah, that's so nice. And it's important. I hear a lot of freelancers say. I've heard photographers and freelancers say, like, oh, I just am so alone. Like, I work alone every day. And I'm actually shocked when I hear people say that because, you know, I joined like a co working club or the Norwood club, you know, and are surrounded by people all the time. Even as a solo freelancer, I'm constantly working with friends or in this online world, working with friends online or doing, you know, so I think it's important to stay connected to our community, whatever that might look like. And that's like one baby step in living an epic freelance life.
Yeah. There's also. There's also so many niche Facebook groups now, like you mentioned, a couple that you're a part of, I've been amazed to see. There's ones for podcasters, there's ones for female business owners, there's one something for every niche topic. And a lot of them go with a podcast of some kind or a conference, virtual or in person. Same as you. I've never once felt lonely. Maybe sometimes lonely as CEO of a business, you know, and not knowing what to do. It's very rare, though. I find that people in the freelance or entrepreneurial world are so down to connect and just help each other out that.
Yeah.
I've never once felt like I was lacking colleagues. In fact, I feel people are more open to just connecting with a complete stranger, which is nice.
Yeah, I love that. Yeah. We have our mutual friend, Dori Clark. I'm thinking of her as one of your, like, colleagues in the industry, probably. Right.
D.C. and Manbon as I call them for short. They were the two that separately wrote back and said, oh, well, Phil is great.
Yeah, they're awesome.
I know.
I like that. And I'm glad you have your community as well.
Well, to you as well, Phil. And I'm so happy you're part of it. Thank you for being in our life. Thank you for the beautiful wedding photos. Thank you for connecting during coronavirus and for being on this podcast.
Yay. I'm so grateful. Thank you for the chat. I love talking to you.
Me too. And everybody I'll throw all the links@pivotmethod.com 227 and Bill, I hope to join for a future podcast club soon.
Thanks so much for listening to this episode of the Pivot Podcast. Make sure you don't miss an episode or my insider tips and templates by signing up for Pivot List, a curated twice monthly newsletter where I share the inside scoop on what I'm reading, watching, listening to, and the latest tools I'm geeking out on. Sign up@pivotmethod.com pivotlist get show notes from this episode@pivotmethod.com podcast and connect with me on Twitter ennyblake.
Remember, build first, then your courage will follow. Hasn't it always.
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