What’s more difficult to achieve: A successful relationship or a successful startup?

Does a startup succeed for the same reasons that a relationship succeeds?
Does your ability to build a successful startup translate over to an ability to maintain a healthy relationship (or vice versa)?
I asked the community a question:
“What is more difficult to achieve: A successful relationship or a successful startup?”
I was surprised with the feedback that I received…
Relationships and Startups are equally difficult
Shane Mac:
I think they are so different but effect each other due to sharing of time/effort… they effect each other but running them is completely different.Federico Imparatta:
A successful startup is like a healthy relationship, especially if you want it to last.
Ryan Paugh:
If you’re in a good start up and a good relationship, they’re equally difficult. Oftentimes for me it’s the conflict between the two that brings the most stress.Where I see parallels
- Emotions battles: You vs. your girlfriend; You vs. your team
- Loyalty and dedication; don’t spread yourself too thin and maintain focus on one thing to gain maximum results
- Pressure to marriage; pressure to work towards an exit
Anne Good:
Both take work but in different ways. Spouse/family should come 1st at the end of the daySkot Carruth:
They are equally hard, and equally harder if you are trying to do both at the same time
Relationships are more difficult
Carlos Miceli
Your guess would be wrong! My first company is doing pretty good. Relationships on the other hand… Healthy is subjectiveJonathan Mead
Relationship, hands down — it’s not even a close to being comparable.Christopher Click
Ha, definitely has to be a healthy relationship, but maybe compare failed marriage rate vs. failed business rate???Grant Stanley
A healthy relationship. I can write a business plan for a start-up. My girlfriends just hate it when I try to write a business plan for our relationships.Brian Linton
Tough question - healthy relationship is harder. My girlfriend and I work together on the startup right now, which makes the relationship even harder sometimes.Andy Drish
Most startups are built in hopes of selling it at some point. AKA - there is an end goal. But relationships don’t have any sort of end goal.
Startups are more difficult
Monica O’Brien
Successful startup - but I have a great husband, so I’m not so partial![]()
Financial Samurai: Once you’ve found someone to spend your life with it gets easy and everything comes unforced. A startup is infinitely harder!
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Can you succeed without trying?
In a startup, there will come times when you have to do things that you hate doing: sales, coding, or networking at an event. There will come times that you have to survive off of Ramen noodles or fire an employee to conserve cash flow.
You have to put in hard work, time, and a lot of effort to make a startup successful.
On the other hand, my relationship with Kim is effortless - we don’t have to try to make each other happy or try to make the relationship work. We just are and we just do, and who we are and what we do makes us very happy.
Monica, Samurai, and I have found that special person that makes love easy.
Is there a special formula that makes a startup effortless, similar to how my relationship with Kim is effortless? I believe the answer is NO, and is the reason why I feel startups are more difficult than relationships.
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What do you think? Have you been more successful in your relationships or in your startups?
Is it possible to build an effortless startup?

















You bring up a great point Jun, I’ve found my relationship with my girlfriend effortless (everything just flows, with a few minor arguments but we resolve them), its almost scary at times, but I realized how lucky I am. She’s starting her own business this summer so its great to have an entrepreneurial minded girlfriend as well.
So far everything is great in our relationship and I can’t wait to add my two cents in her business model but at the same time let her be the captain of the the ship (I’ll just be an advisor and let her make the ultimate decisions).
That sounds so great Tony!
What kind of business is your girlfriend starting?
Are you graduating this year?
Yes Jun, I’m actually graduating tomorrow - awesome the time is finally here. My girlfriend is starting her own leotard line for ballet dancers. She’s going to start with a children line and work her way up to adults.
I have to agree with Samurai - if you have the right person, a relationship just flows. I have had businesses that did the same. I have had other, equally successful ventures, that did not. They took enormous effort from everyone involved. Overall, I have to say that the businesses were a lot harder.
Hey SMU Cox MBA (if that’s your real name),
Thanks for the comment. Tell me a little about your businesses.
What was the difference between a startup that took a lot of time and effort and one that just flowed smoothly.
How can a young entrepreneur best position his or her company to be easier than harder?
Damn….I was trying to stay objective…hope Cath doesn’t read this
Personally, my girlfriend in large part propels me forward and helps me gain a sense of accomplishment that I sometimes with hold from myself. She truly is my “business advisor”
Wow, that’s great to hear Brenton!
Kim is more of my companion away from work. We usually don’t talk about business, startups, or careers; instead, we just focus on each other.
It’s kinda mushy, but it works well with us.
Looking forward to hanging out tomorrow!
PRessure on marriage.. don’t worry. Make sure she reads or re-reads “How To Get Your Super Motivated Boyfriend To Marry You”, and you’ll buy yourself several more years!
Hey Jun,
Personally, it depends on the compatibility of the people involved. If you’re with the right person, where everything clicks and you felt like you knew each other forever when you just met, then the start-up’s going to be infinitely harder (as in, it requires more “work”). The less compatible people are, the more “work” seems to go into their relationship just to keep it afloat, and that’s where your relationships start feeling more like a business rather than a good, loving relationship.
Basically, everyone who responded is right in their own way. Maybe the real question is this: what’s harder - finding someone you’re really compatible with or running a startup? I’d wager that the two are about equal in difficulty.
I say they are both equally tricky and equally hard to get a good one and keep a good one.
Cool post Jun. I know this will be an unpopular comment, but I really think that if your relationship is harder than building a company, you probably aren’t with the right person. When I worked at a startup my relationship got BETTER, not worse. And now, I don’t even see my husband that much with the job I’m in, but our relationship is still a million times easier than helping build this company.
interesting, keep posting!
Jun, sweet! I guess we’re pretty lucky then, as we share the same thoughts on relationships. I’m not sure if my relationship is effortless, but it’s certainly easier than trying to build a business!
However, comparatively speaking, my relationship is effortless compared to trying to build a fortune.
How’s your businesses doing btw? Would love to hear more insight as being an entrepreneur is fascinating!
Best,
Sam
This is a great, great question. I tend to lean towards Monica & Samurai’s viewpoint, that a healthy relationship is easier to build and maintain, so long as the person you’re with is understanding of the time and energy that you’re investing into your business. That said, if the person you’re with isn’t supportive or requires more of your time and you’re being put in a position to have to choose between the relationship and your business, then this becomes a huge issue. That being said, that’s something you’ve got to deal with in terms of all of the people that are close to you in your life; friends, relatives and that kind of thing. I’ve learned that the ones that truly care about you will be the ones that understand what you’re doing and give you the time & space to go after your dreams.
As for the other question, NO it’s not possible to build an effortless startup. Not even close!!
-B
Definitely relationships are way more difficult. Taking action and applying focus consistently you can make a start up succeed. A relationship has too many variables and “feelings”.
I love the way you keep coming up with great content. Really need some of your inspiration.
My thought is that they are equally challenging. A start-up after all is a collection of relationships!
It comes down to FOCUS … which is more important to you at that time.
It is harder to have a successful start up without the support of a understanding partner. If you choose to have the start up any way without the support of your partner - then your relationship suffers. (talking from experience)
The best way to have success in both a relationship and a startup is to be on a journey together where you agree to support each other. (yet to experience - but believe it possible)
Everything is Quantum Physics - what you give your attention to is real. Nothing is objective - everything is subjective.
nice post….. I totally agree with Espree,
To start a Relationship is more difficult. but feelings in any relationship play an important role.