Dating as a Startup Founder

Have any founders tried to actively date while growing their companies? I'm struggling a lot with this, especially when I'm in the early dating stages using apps and doing a lot of messaging and first dates. Unlike my last career, this job seems to be really attractive to men that I meet. The problem is they always ask what my startup does and seem to want to drill down a bit with follow-up questions - it feels like I have to pitch my startup whenever I'm on a date!

Of course it's much easier when I'm in a relationship and the person has the full context (at that point they are like any of my other friends who keep up with my life/career). But unfortunately early dating can be a loop where you go out with someone for a few weeks or months and then you're back at square one again re-introducing yourself to a bunch of strangers on dating apps.

Has anyone come up with successful strategies for dating to not get emotionally drained from dates? Are you able to easily change the subject to other topics that aren't work, or do you lean into explaining your work at the beginning to get it out of the way? I understand because I usually also want to know about the careers and ambitions of the person I'm trying to date, but I'm trying to figure out how to make it less exhausting.

I would just put dating off altogether and say, "I'm going to be heads down on my company for a while and take a break from dating." However, that's basically how I got into this mess in the first place (there's always an excuse to ignore dating to focus on career and only existing friendships). I don't really foresee a time in my future when I'll be less busy, so I'm going to continue dating. Any tips would be appreciated!

MWags's profile thumbnail
Hi Erika! I haven't been in this situation personally but I can see why it would start to feel more than a little draining.I wonder if you could set up a rule on early dates, like "no work talk until X date". You could make it all mysterious (try to guess my job without looking it up!) or just be super upfront, a start up is a LOT of work and one of the things you look forward to about dating is stepping back from that for a little while. I hope that helps and good luck!
Thanks for the ideas! The "mysterious" one would be hard to pull off since Bumble, Hinge and other apps prominently feature your job title and company (I keep it vague by saying "Founder at Startup" or "Working at Tech Company"). But I can definitely try out the "no work talk until X date" and being upfront about how I like to take a step back from my work in my personal relationships.If you are partnered, is there any chance you'd be willing to share how you met your partner? I'm always interested in hearing success stories 😀
MWags's profile thumbnail
Happy to offer thoughts! -- though I'm definitely a bit of a derp at online dating (as you can tell). I am partnered! I'm engaged to the weirdo of my dreams (someday, COVID permitting we'll actually get married haha). We actually met playing co-ed, softball at our company. I played the outfield and he played infield, and I like to tell people that it gave me an excellent view of his rather attractive backside (bonus, it makes him both grumpy and secretly pleased).Jokes aside, online dating can be *awesome* for expanding your pool of people to know and date-- I know several people for whom it worked out, even with lots of ups and downs along the way. But I also am a big fan of making time for playful hobbies as a way of meeting people, especially if straight dates are getting more draining than fulfilling. Obviously I'm biased by my own experience, and my particular hobby being a sport skewed the numbers in my favor, but it is really nice starting your relationship with a shared experience and interest.
Interesting! Unfortunately I keep working in male-dominated environments and having female-dominated hobbies. I think I need a researcher to analyze all of my hobbies and tell me which one to lean into to meet men 😃 (yoga and calligraphy might not do it).
MWags's profile thumbnail
Haha yeah, i kept finding myself in the opposite - female dominated workspaces (mostly media!) and male-dominate hobbies. But if you do meet a guy in calligraphy, it would be like the jackpot lolGood luck though!!
christinamorgan's profile thumbnail
Hey Erika! This really hits home with me as a serial solopreneur/founding team member so I imagine it sits even deeper for you.As an anecdote - I'm currently dating a man who is also in tech, but we spend next to 0 of our time together talking about work, and it's so. damn. refreshing. Of course it comes up sometimes and we're there for each other in that way when needed, but we created the boundary up front that our space is for expressing and sharing other sides of ourselves, since the "work" category is checked off in spades outside of "us." Since your partner's career and ambitions are important to you, it sounds like it probably is important to bring yours up at the beginning, but I agree with Meaghan's suggestion to try something to the effect of "I'm a founder of a startup in X industry, and it plays a huge role my life. In dating/partnership, I'm looking for someone to enjoy life/share X hobbies, interests/laugh, play etc. outside of that world with to stay balanced, so I like to keep it mostly separate until we see how much we can make each other laugh (or whatever relationship value is important to you!)" I might even add a playful - up for the challenge? ;) - since (ime) it is a real deviation from default mode!Drawing the boundary up front can set the tone for the whole relationship to give you what you're actually looking for. And if they cross it - you've learned something even more important before investing any more of your time. We're rooting for you!
Thanks Christina! Interesting suggestion to lead with my job in my bio (plus the boundary-setting phrases). That would actually probably be the most honest thing to do. Right now, besides listing "Founder at Startup" in the title line, I tend to only mention my non-work interests and my full career gets sprung on them during the first date, so it's probably at least a bit misleading!Have you ever actually used the "Up for the challenge?" question in an app? I see that a lot on men's profiles, and I usually assume someone who would write that would be a jerk. But perhaps I'm wrong!Also, congrats on finding someone who never wants to talk about work! How did you meet?
christinamorgan's profile thumbnail
Oooh… I lean cheeky and am a big fan of playful banter, so hadn’t thought of it as jerk-ish. 😁 There is probably some element of “depends on the energy behind it” in that one. Have used in chat, but not the bio itself. Although I wouldn’t be opposed to it bc it’s my natural language. Met this one through mutual friends a few years back and reconnected recently. Definitely counting my blessings about it. Good luck!! 🧚‍♀️✨
lynchen's profile thumbnail
Hey! This is definitely something I thought about a lot previously. I met my partner of 5 years on Tinder (they are not in startups but appreciate it). Went on a few bad dates on the app so I didn't have any high expectations. However, I think something that's helpful is spending more time asking about personal values and interests of your date. Try to learn something new from your date - everyone interesting has something nerdy/geeky about them that they're absolutely obsessed with. You can ask very directly even like: so what's something you love that you can talk about for hours?" Perhaps yours might actually be startups but if you're having trouble going beyond it, I personally would take some time to write down things you enjoy talking about other than startup so you remember to bring it up. A great transition is if startup does come up, say something along the lines of : "yes I'm doing this, and the reason I'm doing this is because I was inspired by...". It's a great way to bring up personal values and deeper topics.If you're for example going on a more creative date like art or cooking together, naturally your focus will be on other things. And because being a founder is extra busy, I spoke out by date three my expectations and values in a relationship. Best of luck you got this girl!!
I'm SO glad you responded! It often seems like all of my friends met their partners at school or through mutual friends in our social circles, so it's refreshing to hear about a long-term relationship that started on Tinder (I'm glad to hear from @applecoffee about meeting her partner on Tinder too!).You are right, I do have many nerdy/geeky interests. And definitely the conversations go best when I only touch on my startup's mission and why it was significant to me. I'll try to be more conscious of shifting it from that direction into other things I want to talk about!When you mention bringing up your expectations and values by date three, what do you mean? No need to answer if it's too personal. I do tend to try to figure out all of the dealbreakers as soon as possible (e.g., do you want kids, where do you want to live long-term, etc.) to eliminate incompatible people so we're not wasting each other's time.
lynchen's profile thumbnail
Yep! first layer of personal values like political, religion,and expectations from a partner. Even things like long distance - some people are okay with it and something people are not. Personally I think it's good to know what you want on a deeper level (ie kids or even pets) but these things are unpredictable and can always change so it's best to talk about it with your partner on an ongoing basis when trust and basics are established :)
applecoffee's profile thumbnail
Hi Erika! Dating can be exhausting regardless if it’s done online or offline. After an unsuccessful marriage, I spent 3 years on Tinder and was actually able to really enjoy it. I took it like human research (my background is in design research), and I was really genuinely learning to know people without an agenda to find a partner (although yes I really wanted to meet a life partner). One thing that I loved pulling out on my first dates was the ‘36 questions that lead to love’. Google it or here’s an article that explains it. approached it very casually and asked if they’d heard about it. Most guys were intrigued. The first time I used it, the guy googled it himself and wanted to get straight into it. He then raved about it to all his male friends afterwards. The beautiful thing about these questions is that you very quickly learn things about the other person that you’d never learn on a first date. And as it’s a framework, not your own questions, it doesn’t feel like you’re probing too much. I ended up finding my now partner, a wonderful guy and we already have a 2 year old too :)Good luck! Enjoy the process and take breaks if it gets too much.
HannahShtein's profile thumbnail
Hi Erika! I don't struggle with this particular issue, but I worked with an amazing dating coach who specializes in high-powered + CEO women who is great at helping you handle these types of situations in the dating process in a way that feels good for you. Feel free to message me if you want to chat more about it / it sounds like it might be helpful for you (I don't get commission or anything lol, just love the person I worked with!)
cynthiaro's profile thumbnail
hi Hannah! I'm going to DM you also. I refer a lot of my clients to date coaches, and would love to learn about your coach so I can potentially send her some folks!
HannahShtein's profile thumbnail
sounds great!! she's awesome
Do you know what she charges? I'm not "high-powered" in a way that I make very much money, haha. When I hear about dating coaches and matchmakers, I assume $$$. The apps are a free DIY solution (plus I've ended up in a few serious relationships with people I met from apps).
HannahShtein's profile thumbnail
She has multiple options - I did a 3 month group program with her which was $5k and totally worth it in the way it upleveled my mindset, confidence, and communication skills around dating
Hi Erika75! I have an idea and don't know if this will work. May be you can say you are working in a company (that happens to be your startup) and don't give all the details. If he searches you online and find you are the founder of the startup, he will ask why you hid it from him. Then tell him the truth. You don't want your work to be the topic for discussion and you are looking for a partner that does not feel intimated and not attracted by your job. Tell him the truth. This way you know whether he pays attention to you as a person or not. If he becomes rude and defensive, you know there won't be another date . If he is sweet and does not talk about what you do in the coming dates, you will know he has a genuine interest in you.