In today’s episode, we talked with Holly Diamond, Founder of Work Onward, about her transition from education to recruiting to standing up the world’s most intuitive career marketplace.
In today’s episode, we talked with Holly Diamond, Founder of Work Onward, about her transition from education to recruiting to standing up the world’s most intuitive career marketplace.
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Hatchet Ventures website: https://www.hatchetventures.com
Hatchet Ventures LinkedIn: https://www.linkedin.com/company/hatchet-ventures/
Chet Lovegren’s LinkedIn: https://www.linkedin.com/in/chetlovegren/
Connect with Holly Diamond on LinkedIn: https://www.linkedin.com/in/careerdhd/
Check out Work Onward’s Website: https://www.workonward.com
Listen on Spotify: https://tinyurl.com/36ub3fpy
Listen on Apple Podcasts: https://tinyurl.com/ystuxubt
Listen on Google Podcasts:
1, 2, 3, 4. Are you a founder, co-founder, aspiring entrepreneur, or just someone who loves to hear about how companies are built? Then join us as we talk with founders and CEOs who have been there and done that. Welcome to the Founders Formula Podcast. Sponsored by Hatchet Ventures and now your host, Chet Lovegren.
[00:00:32] Chet: Hello and welcome one. Welcome all to the Founders Formula podcast, the show that's designed to bring you the latest and greatest insights from founders and CEOs worldwide who have been there and done that. As always, I'm your host, Chet Lovegren, and a big shout out to our sponsor, Hatchet Ventures for sponsoring today's episode.
I'm really excited about today because today is the season finale of season two. So we've hit our 24th episode. One important thing that I love about the podcast that I've been letting everybody know is that, 90% of podcasts. Don't make it past episode three and the other 85% from there don't typically make it to episode 25.
But if you include all the episodes that we put together, we're there, we're well past it, and we're on our way to recording season three, but enough about that. Because today is season two finale and I'm really excited for today's guest. She is a Hatchet portfolio member. She's a career consultant with a background in recruiting and education.
She's also a restaurateur of the best dang restaurant in New York City. Mistah Oh here to talk about her company today, WorkOnward. Please welcome Holly Diamond. Holly, how are you doing?
[00:01:39] Holly: I'm doing fantastic. How are you?
[00:01:42] Chet: I'm doing well. I'm glad we could finally make it work. We've had a little bit of scheduling conflict back and forth.
The beginning of the year has been really busy for everyone. But I'm glad that we're here today and we're gonna talk about you and your company and then some insights on your journey as a founder, and then some of the ways in which you're working with Hatchet as you approach investors. We'll dig in.
I'm not gonna, I'm not gonna spoil the surprises for everyone the show. Into the show, that first we like to kick it off with a little insight on who we're talking to. I highlighted that you have this experience in education, moved into recruiting, then did career consulting as well as your experience in the restaurant space, being a small business owner of a restaurant in New York City which Holly told me that she's gonna gimme a free meal.
If I make it out to New York City, she's gonna treat me to a free dinner. So I'm pretty excited for the next time I'm in New York City, cuz I'm a pretty hungry person most of the time, so I know it's gonna be great. But fill the listeners in. Let's talk about Holly Diamond.
Let's talk about your experience up to the point of founding your company WorkOnward.
[00:02:45] Holly: I studied psychology back in University of Oregon. And when I graduated, that was back in 2008. And if some of you remember back in 2008 it was an economy recession. A lot of people are having hard time finding a jobs.
I ended up moving from Oregon to New York. Tried to find a job the challenge that I had was I didn't have a job, a place to stay or any friends or family members. So it was just all me when I first moved to here, which was a very scary experience when you just graduated from a school. And my career aspiration wise, I I always wanted to become a psychology professor.
So I was on my way to studying, to apply for the PhD program in Cross culture, psychology and it didn't work out due to the financial challenges. And what I did was I moved back to Korea where I originally came from and I ended up teaching English and Korean students and then winding up going to the graduate school, continue to follow my passion to become a professor.
That journey didn't work out either. So when I came back was it back in 2015. Just over a over a decade ago, the first job that I got was a recruiter. So I start working as a recruiter for a small recruiting agency, and then ended up moving to a larger recruiting agency located in New York.
After that, I during the time when I was working as a recruiter I I couldn't give up with my dream, my education dream to become a professor. And so I was thinking about how can I merge my professional experience as a executive recruiter. And then still pursuing my educational content in psychology.
And then if you combine the recruiting and charter helping profession it was a social work. So I going back to the graduate school again for the third time ended up in the Fordham in graduate school, in the social work program. My mission at the time was to try to help people find these jobs as a recruiter.
The recruiters, we work with corporations and enterprises most of the time, and my heart really belongs to the job seekers who keep getting rejected because of their background. And I thought that just makes sense, right? Studying social work and then becoming a social worker, try to help people find the jobs in the public agency.
And so the funny thing was I never really planned to become a business owner startup founder, or restaurant owner owner at all. Everything happened almost naturally. And when I was a part-time graduate student in the social work I still need to have a job. I ended up opening up my recruiting agency.
Starting from the basement of my in-laws house in New Jersey. So I was going for the part-time graduate school and then also working try to, pay the bills and then I tuitions and whatnot. And, doing my own recruiting gig as the recruiting becomes busier and we started getting more clients and becoming a little bit more successful, I realized that I couldn't operate the business by myself.
I need team. And I was navigating about do I want to make it a little bit bigger or just just be happy where I am. Just a one person operating the recruiting agency. And I was asking somebody that who's been operating a recruiting agency for many years. All by herself.
She's up in the Massachusetts, so I was asking for her advice. I didn't know what to do at time. And as I asked her advice was Don't hire anybody because this ended up giving you a lot of headache. Managing a people is not an easy job, and if you operate the business as a one person shop not only you would collect all the commissions all by yourself, but you'll be stress free.
Because you're de you're not dealing with the the employees or the payrolls and things like that. And, when I listened she, her advice I ended up doing complete opposite. I said, screw you. I'm going to hire people. I need the helpers. I can't do this all by myself. And looking back, I think this is a probably the best decision that I made because if I didn't have a people building this company together with me I wouldn't be here where I am.
So the advice if anybody's listening to this podcast it's just because somebody has many more experiences before you, doesn't necessarily mean that they're paving your path. You have to follow your gut and go with it. And yeah, that's how my founder journey started. I that by the time in 2019 luckily right before the pandemic so I opened it, I ended up opening on my own recruiting agency.
By the end of the 2019, I had about two people that I hired and one person actually still working with me as a marketing manager in our company. And as a company is growing, I start to add more people.
So next year, from the two people working on helping the building, the company together ended up becoming 10 people. Now I'm currently managing about 15 employees building the company together. So yeah, I guess that's my journey.
[00:09:17] Chet: That's amazing. And I, what I really like about it is your ability to be adaptable.
Hey, I was pursuing this thing to be a professor, didn't really go the way that I thought it was gonna go, so I'm gonna go do this thing that I think can further facilitate my passions and my desire to help people. I need a little more schooling for that. I'm gonna do some more stuff over here.
You know what I mean? Further my education. And then as you even said, like I had to do things along the way to pay the bills so I could do what I knew I was destined to do. But that resiliency and that adaptability, I think you hit on some important things there are really important lessons.
And traits that people need to have if they want to be founders. Because you have to be adaptable and you have to be resilient because things aren't always gonna go your way. It ebbs and flows. It's one of the reasons I find the go-to-market leadership space so interesting because I'm constantly seeing, average tenure is 18 months of a VP of sales in my industry.
And it's so interesting because what do you just check out when things don't go well? Like I can tell you that if you ever want to be your own founder or your own entrepreneur, like that's not gonna work because you have to ride the ship out. You can't just close the company when things don't work well for you.
They don't go your way, especially when you have people's livelihoods depending on you. But no, I love that story. I think that's a great testament to your traits as a founder and the social and philanthropy side of what you're doing at WorkOnward. Let's talk a little bit more about WorkOnward.
How did you get the idea for this company? What is it that you do? Who are you helping? What's the problem that you're solving? Give us the background on the company. The company highlight. And then let's talk a little bit more about the story of founding the company and some of the things that you've learned along the way from your experience.
[00:11:07] Holly: Yeah, I love that. So I guess, like I mentioned, I never really planned to become a startup founder. I didn't, I'm not a technical founder, obviously, so I didn't know how. Build a company WorkOnward is hr tech is. It's HR platform to help small business owners find local talent easily.
I guess the journey of our story is starting from the rejection. Rejections me as a job seeker rejection, me as a small business owner, and then the rejection that I, work with candidates through the recruiting experiences for the past eight years or so. I was, constantly, I found myself constantly complaining.
Every time I meet somebody, I've God bless my husband and my family. I was complaining nonstop When candidates get rejected, I really agonize the pain with them because I have similar experiences and especially in this market where is you see a lot of layoff posts on the LinkedIn, on Twitter and it the rejection it linger, it lingers it doesn't go away easily.
Your past experience, you getting rejected for your first job, your dream job, and you are working really hard for this company and the next thing you know was you are replaced whatever reason would that be. And so the rejection always stayed. And by the time I finally decided that, you know what, I don't think there's any platform out there to help people who get rejected from a job.
How can I try to find a job for them, right? That's my job as a recruiter. I try to help people find a job, but at the same time, I have to make a placement for the companies that we partnered with. And and traditionally in the recruiting space, we are called as a head hunters, we're hunting talent, right?
And we are trained as a recruiter to find one person to fill the job, which also means that you get tons, sometimes thousands of applications, a lot of people looking for a job. People apply jobs and as you navigate and they go through those resumes, you have to constantly reject them until you find the best person to fit into that job.
And I think there was a dilemma that I had. At one point I have to make sure I find the best talent and make a placement to keep going with the recruiting the successful and then keep up with the KPI at the same time. I ended up rejecting 99% of job seekers that couldn't fit in the job.
And as a recruiter, you are a human, right? You have a conversation with the job seekers and you go through interview process with them, and then you start to realize that those people have stories, those people have challenges, and they're not just a piece of resume, the Word doc or, the PDF of resume.
They have a voice. And there's a reason, why they're actively looking for a job. Maybe they're desperately looking for a job. I had so many painful experiences. So when I help those job seekers and I try to find the job if you constantly get rejected, you apply jobs and you don't hear back or you get it rejected for whatever reason.
Most of the time it's because your resume is not aligned and those particular group of people that whose resume is not aligned are typically overlooked. Job seekers, when I mentioned overlooked, there could be somebody who's overqualified, somebody who been in, in, in their profession for 20 years 25 years, and nobody's hiring them because they're overqualified.
Sometimes you have a criminal background, sometimes you are, immigrant or woman, whatever the situation that you are going through. And that doesn't have to be, somebody coming from the background or whatever situation you are going through when you can't, get a job.
I think that I really resonated with that the darkness that the people go through. And I finally realized that we need to have a platform that really brings light to people in the darkness especially that, you are looking for a job and you don't get the answers from the hiring managers when the jobs that you applied.
So that's WorkOnward. We try to increase the visibility of job seekers and small businesses, so sometimes you don't even know that they're hiring. And if you walk around the street and then you see that open jobs and we're hiring on cardboard and, just sticking into the window of the storefront.
Nobody knows you are hiring jobs, right? Unless you're walking by. And so what we try to do is how can we make them more visible? How can we make them seen? And the solution that we came up with was what if we use geo mapping feature such as Jira? When you, you go to our platform and type up the the zip code, and then you really umi digitize any local jobs on the map when you are, if you are a job seekers within that area the local communities people can find you easily based on the the map.
And so we, we try to connect, we try to make a direct connections between the job seekers or having a hard time finding jobs on their own. And then the business especially for the small businesses that they can compete with the larger corporations to try to attract the talent. Or they couldn't afford to use recruiting agencies or.
They're not technical to use some of the HR softwares and then try. Make the connections more easily.
[00:17:42] Chet: Yeah. Plus the concept of a marketplace is a lot easier for people to grasp than even just like my experience with Indeed or ZipRecruiter as a hiring manager trying to navigate those platforms.
Or LinkedIn. Which LinkedIn is more like, your local mom and pop small business is probably not on LinkedIn for the most part, but they are posting on Indeed and ZipRecruiter and it's tough even for someone who's worked with HR software to try to navigate them and work through it.
And what I also love is with the geo mapping, it sounds really cool because you're almost creating a sense of community as well. You're working with people in like-minded areas, but above and beyond that, what if I'm a single mom and it just really lines up if my job can be in the same neighborhood as an afterschool activity I'm taking my kids to, or a place where a relative lives that are watching the kids after school or something, like you can really map things out and make it easier for the job seeker to find a job in a place where they might not have found a job before.
Right. And that jobs that that company as well, that small business is receiving the same benefit where they're able to get visibility into talent and visibility in front of them and creating awareness that, hey, we are hiring that they may have not gotten before. So I really like how you're creating that sense of community, that tribe for these people.
That are looking for places in their area. Cuz the thing that kills people is the commute, right? Like the commutes are terrible and sometimes we do, we end up working. I had a job once upon a time where I was about an hour and a half from my house with LA traffic, and it was every day, an hour and a half each way.
I call that nine month stint my education though, because I just podcasts every single day, all day in the car. So it was just a massive amount of learning and audiobooks, but, it's not sustainable. And so you're creating a sustainable community driven way for people to source talent, get visibility into their hiring, as well as giving candidates that same visibility, which is really cool.
I like that. That's awesome. Let's dive a little bit into your journey. As a founder with WorkOnward we called it out at the beginning of the show. You're working with Hatchet, you're one of our members WorkOnward it's a portfolio company that we're working with. Let's talk a little bit about your experience working with Hatchet as you're approaching investors right now, because as I understand it, you've been bootstrapped up to this point.
But now you're in the process of going through a round of funding. You're redeveloping your pitch and your deck and the way that you connect and interact with investors. So let's dive a little bit into that. What's your experience been like working with investors up to this point? And then what are some things you're learning along the way that you think are great insights for founders listening to the podcast to take into their next round of fundraising?
[00:20:26] Holly: Absolutely. Yeah. Like job search process, fundraising if you are underrepresented founders and solo founders, booster founders, whatever founders you with a label to it it can be a very daunting, and lonely process. And that's been my process. I did not know any lingo, with the CAC or the PMF and MVP.
I did not know any of that when I started building a software. And so having that community is definitely, is the worth the journey again, going back to the same concept of when I was debating whether I should just keep going at it by myself or ended up, adding more people to our team and then building the company together to become a little bit more sustainable.
I Hatchet Ventures has been the the community that the supporters and the cheerleaders. I we have a weekly the meeting and just follow up about my progress. Some of the success, some of the challenges and the fails as a founder. And then they're all founders before they all work in the startup industries before.
So they get it, they get the pain and frustrations and the rejections that you are going through and it's almost having a good group of friends that you never met before cuz we're all working from, the remotely, but then somehow they just get you. And that's something I am just really thankful to be the part of the Hatchet community and the Angel from Cuemby the team they did the last episode he was actually the person introduced me to Holly check this the Hatchet Ventures out, they're doing something cool.
I think that you will get a lot of benefit from this and. I had a lot of doubt at the very beginning. How can they help me? What do they want? I now hindsight it was a best decision that I, one I trusted Angel there's always backing up for me. And then two I have a just group of the supporting group of people that I trust through this journey.
[00:23:00] Chet: Yeah. And that, I think that speaks miles when somebody that is working with Hatchet refers another founder into Hatchet. And it's just a great, and even me as a founder, I don't have a software, I have a services based business, but just the feedback that I've gotten and the help that I've gotten with things like, oh, I'm working with a contractor.
Does anybody have a good NDA that they can share? Things like that are so helpful than me trying to recreate the wheel or go figure it out on my own. I want to close the episode with what would be your biggest piece of advice to founders that are in a similar position?
I'm going through fundraising round. This is really scary. I've got some people that are under my employ and, obviously the economic climate is. Not a secret to anyone anymore. Like the economy's really going through it right now, but what would be, from your experience, your biggest piece of advice to founders or the insight that you would share with them as they're in a similar path in their journey?
[00:23:59] Holly: Yeah. No, it's a tough tough time right now for a lot of people, including myself and, many other startup founders. I. Always remembering the first day, the excitement that, finally the aha moment of, you know what? Screw this. I'm gonna build a software, I'm gonna start this startup company.
Because all that frustration that I had remembering that and holding on to. You know why you started from the first place. If you have the right reason you will survive. I think, no matter who, whoever is saying you, you will, meet a lot of naysayers through this journey.
When I first started the startup founder, a lot of people are telling me, That you don't know anything about the tech space. You don't know how to build the software. And you know you have recruiting business you are doing. And I also ended up opening up the restaurant. And the reason I opened the restaurant was to.
Create a job opportunity for my family. It was right in the middle of pandemic and so I was already going through the two different ventures at the same time. So I get a lot of Doubt. Coming from the people the closest family, friends and sometimes even your employees they question you all the time, are we gonna make it, how far how long can you go?
And. Every time that I, I get those self-doubt. Sometimes the, that comes from the other people, sometimes, a lot of times it actually comes from you. So you're dealing with that every night when you are done with the work and then right before you go to bed and all the scary thoughts start to like crumbling.
And whenever that when you are going through the dark moment and questioning, why am I still doing what I'm doing? Always remember the first moment. And that's, that keeps me going.
[00:26:09] Chet: Yeah. If being a founder could be done by anyone, there would be more founders. And so I find that when people project their.
Insecurities on others, it's because that's why they're not a founder. You know what I mean? And that's okay. And obviously, you have your North Star, but I get that a lot too. Chet, why would you go into business for yourself at the beginning of 2023? Have you seen the economy right now?
Have you seen what other people that were doing similar things to you are doing now? They all went back to work. They, they stopped doing their own business. They closed their business and went back to being a W2 employee. But again, the, you're North Star. We had a company I used to work for many moons ago.
Laid off a significant amount of their salespeople and spent about a week just doing some outreach and support with those people and telling some of my former reps some things like, one of 'em I said, Go hit a bunch of golf balls, knock the tar out of 'em, take your wife out to a nice dinner, play a bunch of video games or something tomorrow.
Just be totally lazy. Enjoy your life, and then get back to it on Monday. And he was like, thanks man. I appreciate the support. I thought he didn't really take it too heart. He was just like, yeah, I just got laid off whatever, brush it off. And then Monday morning he posts that text on LinkedIn. It was like, love former leaders like this still reach out to me.
And I would, I texted my wife a screenshot. I was like, this is it. This is why this is why I'm willing to put up with all the other crap, because that means so much to me that I can impact someone's life that way. Similar to what you're doing, like you said, like I took all this stress from the people that I was working with and I was so mad when people get passed over, and these are people that are more than just a pdf they have.
Their livelihoods at stake their, their mindset, all these things, and I just wanna help them. And so I love what you're doing with WorkOnward. I love the experience that you bring to the table in the recruiting world. And I have nothing but respect for people like you that are, I'm diving into the software world.
I'm gonna learn the acronyms. We're gonna get there, we're gonna, we're gonna, we're gonna make it happen. Holly, if people want to connect with you or work onward, what's the best place to do that? Where can they engage?
[00:28:14] Holly: Absolutely. The best place is our website, obviously is a www.workonward.com I'm very active on the Twitter and then LinkedIn.
You can always send the email and then connect with me, especially if you are actively looking for a job. I would love to chime in and help along with chat. So yeah, let us know.
[00:28:36] Chet: That's awesome. And if you're interested in engaging with the podcast myself or Hatchet Ventures any further, we will have links to our LinkedIn profiles and where you can get in contact with us in the show notes, the show descriptions below, alongside access to work onward their website, as well as Holly's LinkedIn.
If you want to communicate with them you know the drill. Every single Tuesday, 9:00 AM Eastern, we release a new episode. But unfortunately since today is our season finale, we will not be releasing an episode for a little bit of time. Chet's gonna go on a little bit of a much deserved break. We're gonna start recording and producing some episodes with our new guests in season three which we will release some more information on when Season Three's debut will be.
We appreciate everybody listening for the past couple seasons. If you wanna listen to more episodes, Spotify, apple, Google Podcast, iHeartRadio, Stitcher, breaker, all the places, wherever you like to listen to podcasts, you can go back and listen to our other two seasons worth of content as well.
After you finish today's episode, we appreciate all of our listeners. We appreciate our sponsor Hatchet Ventures and we'll look forward to seeing everybody on the next episode on the season three debut. Thank you, Holly.
[00:29:45] Holly: Thank you so much for having me!