MY BIGGEST FAILURES AS AN ENTREPRENEUR 😱 (Confession!)

MY BIGGEST FAILURES AS AN ENTREPRENEUR 😱 (Confession!)


– I’m often asked about
what my biggest mistake as an entrepreneur is, and I think it’s an interesting question. I would say that probably
the biggest mistake I’ve ever made as an entrepreneur is how long I stayed a solo entrepreneur and just utilized the occasional project-to-project freelancer instead of getting at least part-time
help and building out a team. I would say that from the
standpoint of personal care I also kind of like dropped the ball a lot of different times
when it came to that. And I don’t think that
it’s that I overworked or worked too hard, it’s that I think that I didn’t appreciate
the mental fortitude that it takes to do this long-term. And I didn’t always give
myself the bandwidth, and the amount of necessary relaxation, or keep up with my nutrition
enough to really think about my mental capacity to
balance all of these things. Then, combining that with
not having other people to prioritize something and to give it the attention and focus it deserves. It meant that there were
areas where I slacked, or I let myself down, or even
where I let the audience down in terms of either not
being consistent enough or not producing, not
I would say my content, but other things to the quality or the standards that I want. Like not being able initially
to have done the podcast as consistently as I would’ve
liked when I launched it. Or the fact that I didn’t keep up with the show notes on the
website for the podcast or even the design aspect of that. Because I had a focus in other things, like my coaching clients,
or the workshops, and consulting, the public speaking. Those things take up so
much of my mental energy, and physical energy, and bandwidth that I was letting a lot of
admin work go by the side, or not updating the website properties, or not giving people
the attention sometimes that I felt they deserved
that I was working with. So I feel that there’s a
real sense of I think pride in knowing that you’re doing things by yourself, you’re relying on yourself. I think self-reliance,
individual responsibility is so much a part of my personality that in many cases
maybe I took it too for. And I maybe took too much pride in that, and was unwilling to let go of things that I absolutely should’ve
so that I could prioritize and focus on things that truly, truly demanded my personal
care, and attention, and even people that I should
have invested more time in. And I feel that this is a
trap that a lot of people, especially content creators or people who they are a solo in their business. And a lot of people, they have to be. A lot of people have to be
a solo in their business for a lot of different reasons. Primary example, I have
a very good friend. She is a single mom, and she
runs a stay-at-home business. And she also has a chronic illness. And the option of like
being a solopreneur, it wasn’t that it was an option. It was that it was the circumstances
that she was faced with when she started and built her business. But the smart thing that she
ended up doing down the road was she ended up getting
a personal assistant and somebody that could
help her part-time. And then she was able
to shift her priorities. For her, that meant like,
well, being at home, and taking care of her
health, and taking care of her kid was her real
number one priority. And it’s part of why when
things didn’t work out for her in corporate she had to become a stay-at-home entrepreneur
in a solo business. But she didn’t have to be in it completely by herself the entire time
because once she had traction, and success, and had some money coming in she was smart enough to realize that she needed to take
things off of her plate so that they could get done to the best of her ability, so she could make the most of her health and the most of her time. And I’ve taken for granted my good health and my good fortune in
many ways to the point of riding the line, not of like
mental or emotional burnout, but physical exhaustion,
or physical fatigue, or overexerting my body, and
creating problems for myself. But, also, dropping the
ball or not producing my maximum potential of
quality in things that I do because then mentally
I’m stretched too thin. I have the capacity to keep
up and to do the things, but maybe not to the best of my ability. So I think that, for me, I think
that staying solo too long, not being willing to let things go, not willing to trust other
people to deliver for me was a barrier to a
greater level of success. And I’ve since kind of adjusted
and corrected those things. So, I think that if there’s a lesson that I want people to learn from that, it’s that you have to not
only attract the right tribe in terms of your people when
it comes to your customers, your following, your audience, you have to attract
the right people to you in terms of who you’re gonna work with. For me, that process was very slow because of my own issues with trust. And some of that is in
my past experiences, but you have to be able
to move passed that pain. And you have to also trust yourself that, you know, this is not gonna be so bad. And you have to really,
like, not be doom and gloom about the worst case scenario with that. It sucks to be let down, it
sucks to be disappointed. No one likes to feel
that, and we certainly don’t like to feel rejection,
but those are just part of the process of building
something successful. There is going to be pitfalls,
and failures, and setbacks. But they’re really learning opportunities, and they’re developmental
opportunities to grow. So, for me, I think that there are parts of the process where I accept the pain. And I think there are parts of the process where I was practicing avoidance. And, for me, I think that that represents my largest overall mistake. I think, for me, the largest
mistake was not recognizing that there are people who want to help me, and that can contribute the
value that I’m looking for at the level that I’m looking for. And that I’m just not
giving them the opportunity, and that I was rationalizing that, oh, I can do it faster, or I
can do it just as well. Or I can do it on my
own, I’ve been doing it on my own all this time,
when that’s not something that needed to continue as long as it did. And it’s not something that
I had to put on myself. There were people more than happy to help. And I just wasn’t open to it. I wasn’t looking and
seeing the value in it. And I think that you can make an argument that some of it might have been pride, but I really just believed
that most of it was just fear or pain of past experiences
much more than it’s pride. I think that pride became
the rationalization. And I think that a level
of what could be argued as overconfidence in the ability to get everything done all
the time became a liability. And I think that that’s something that you don’t have to go
through if you understand that what you really need to look for is to look for people
that have proven to you that they have your
best interest at heart. People who have not really
asked much or anything of you, but have kept trying to give,
and give, and give to you. Those are the people that you
want to give opportunities to, and trust, and that you want to work with. Also, be willing to reach
out to your friends, and to ask them how they are doing things. I think sometimes we
don’t want to look bad. I mean, not me because I
ask my friends all the time. How’d you do it, how’d you
do it, how’d you do it? What’d you use, what’d you
buy, like who’d you hire? I try to do those things all the time. Most of the freelancers that I’ve ever worked with were referrals. If it wasn’t somebody who
hustled from this community, like for free to get my
attention, and then I hired them, then it was often referrals
from people in my network of someone that they
thought would be a good fit. And having the right people
around you that know you and know what your personality is is where you’re gonna get good referrals, and resources, and things like that. Because then those friends, or colleagues, or contemporaries, they know you, they have your best interest at heart. And they also themselves don’t necessarily want to give bad advice or bad referrals. So they’re going to connect
you with the right people. So I think that having people who look out for you is the best. And you might not have that right now, but your vibe attracts your tribe. And if you keep putting out work, and if you keep showing
people who you are, then other people are
gonna show up for you. And other people are gonna
gravitate towards you. And then you’re gonna be able to build those relationships, as
long as you allow yourself to be open to it and
to be vulnerable there. I know it’s hard because,
again, it’s hard for me. Like, I’ve had very bad
experiences partnering or working with people
many, many, many years ago. And I think that some of those scars sometimes make me hesitant
in areas that I shouldn’t be. So it’s a lesson even for me. A lot of people have
asked over this video, they want to know where I was like what was your biggest mistake? And it’s very hard for
me, not because it’s hard to admit mistakes, at least
not for me in that sense, it’s hard to recognize them as mistakes. Because I’m just so
grateful for where I am, and what I have, and the opportunities that I don’t look at those things as much as mistakes or
things to dread as much as part of the process and
part of how I’ve learned. But I think for all of you hearing, well, what was your biggest
mistake is motivating, or it allows you to relate to something. Or it’s a learning opportunity for you. But I just try to not regret those things because there’s no point
in dwelling on them. And learning those things and
having those painful lessons still got me where I am today. So I don’t choose to
acknowledge them as mistakes. I look at them as growth opportunities or learning opportunities. I either win or I learn, I
don’t lose, I don’t take Ls. I make it a very important part
of my life to say I refuse. Like, ’cause so many people, there are some of you watching this, you find every excuse and every reason to snatch defeat from the jaws of victory. Like winning is right there for you, and you still find a way to
quote unquote lose somehow because of limiting
beliefs or things you have. It’s like people are
literally trying to slap you in the face with a W, but
you’re just reaching for that L. You have to have it somehow. So, I think that there
was a point in my life where I could say that
was probably me too, so I’m probably projecting. (laughs) Yeah, but today it’s very hard
for me to call it a mistake because I think it was part
of the process of growth. And I think that growth sometimes is going to require a little bit of pain. And that’s what growing pains are. I mean, that’s just the way it is. That’s my experience, that’s
like the quote unquote biggest mistake I ever
made as an entrepreneur. Question of the day,
what is the most painful but most valuable lesson
you’ve learned in your career, or your journey, or in your life? Let me know in the comment section. Like this video if you like
it, don’t forget to subscribe. Check out the other awesome
stuff here on the channel. As always you guys, thanks
so very much for watching. And don’t forget, go out there, and create something awesome today. Go make some mistakes, take care. (soft rhythmic instrumental music)

100 thoughts on “MY BIGGEST FAILURES AS AN ENTREPRENEUR 😱 (Confession!)

  1. #QOTD: What is the biggest failure that taught you a valuable lesson?
    BTW: If you could listen to the PODCAST on Apple and leave a rating and review if you enjoy it that would be Awesome!
    http://robertoblake.com/itunes

  2. One thing I've also learned is that you shouldn't just be consistent and patient. You have to try to improve your new video and make it better then your last even if it's by 0.001%

  3. Loved your last two videos. Loved hearing your thoughts. My biggest failure so far was not starting sooner. Thank you for the candid words and glimpse at things we can correct earlier.

  4. It’s great to have some inspiration on YouTube when there’s so much drama. Thank you for another great video!

  5. Wow, Roberto I really like the style of these videos you been putting out. I'm surprised at how comfortable you are sharing your shortcomings and in a sense getting an inside look inside who Roberto Blake really is and how much you care about others in your audience whether they appreciate the message or not.

  6. #QOTD: I'd have to talk about something that happened very recently. I started suffering some hip issues from sitting too much and working on my freelance work, to the point where I couldn't sit for more than a few moments without being in pain. So I had to force myself to go out for daily walks and to ice and do stretches to make sure my hips aren't tight. Thankfully I can sit down just fine now, but the hip pain still lingers on, so I have to keep at it and it'll go away in a few weeks (hopefully). So yeah, don't take your physical health for granted. Take care of yourself, even if it's just going out for a walk.

  7. Wow, thta is pretty deep. Very inspiring. Thanks for the insite and knowedga for the small, new you tubers like our channel, Lima Bean TV! Thanks again you rock!🙂

  8. My biggest lessons are one try as hard as possible. Two, feel the pain of failure but adapt and try your hardest again. And my biggest lesson is, your happiness cannot be at the expense of someone else’s happiness. Everyone has the right to pursue what they feel is good for them.

  9. Your videos are awesome! ⚡
    You inspire me to create similar videos on my channel 😊 Business, branding & social media are simply so interesting to learn! 👌

  10. love your content..amd your videos….the leather cap and hoodie are making me sweat…u know its summer time..lol..keep up the good work

  11. I would say my biggest failure that taught me a valuable lesson is when I wasn't in the right mind set and got to a darker place that I didn't want to go and try to remember now not to drift back to that point mentally.

  12. Great video Roberto. I agree that you can look at mistakes as learning opportunities and as feedback you can use to grow. Keep up the good work.

  13. I have two life lessons that it took me a while to learn, but learn them I did, often the hard way. The first is: "Perception is reality". How people perceive what you are doing or saying becomes reality for them no matter what you meant to say or do. The second one is: "Pick your battles". I used to argue and fight for every little thing and I had to learn to let go of some small things and fight for the important things in order not to be exhausted from constant battles.

  14. I spoke about listening to the right people on Twitter today. There is so much value in having the people who have your best interest at heart. They will not let you talk down about yourself, and will help you see the best version of yourself. Great video man.

  15. I think your content is amazing, great job man. I want to ask you something, what do you think has more value: ¿study, get new skills and degrees or going out there and making your own thing? For context, I am a graduated graphic designer and I'm about to get my degree as a professional on advertising / merchandising but I am stuck because of personal/financial issues, and can't find a job since 2015. People around me are giving me the advice (pushing) to get my degree but I'm so frustrated, I just don't know what to do. Greetings from Colombia, again, amazing content, thanks and keep it up man.

  16. Big failure was spending nearly a decade chasing two degrees knowing they’d lead me to teaching and then I hated the kind of teaching I was “qualified” for and I learned you shouldn’t keep chasing a mistake just because you spent a long time making it.

    Big failure was letting work pile up and disappointing clients when my business was starting to take off. Learned to pace myself and the value of underpromising and overdelivering.

    Every f*ck up is a lesson

  17. Stress is very real! It can be such a deterrent. #selfcare #yourvibe #yourtribe love this Roberto! Keep them coming! 💓🙏🏽🔥🌻

  18. You created something awesome with this video and the thumbnail!!! Well I'm still making so many mistakes, I hope I'm learning from them 😆

  19. Definitely makes sense,taking care of your health along with everything else. Glad you are helping other entrepreneurs with your story Roberto👍

  20. hi Roberto! I'm a subscriber since 2016-2017. I really appreciate your channel and what you share to help and inspire us. I know this isn't related but I came across your video from 2016 (website for graphic designers) and you talked about Bluehost which I'm currently doing research on, but I also saw porkbun.com and what interesting is their pricing and they offer .design in the domain like (www.portfolio.design). I hope you can check that out

  21. I find the idea of embracing one's mistakes because they teach lessons very inspiring. I have to say that the most painful, but valuable lesson I learned from a mistake has nothing to do with any business, but it's that I shouldn't stay silent when someone is abusing me. I could've been saved many years of suffering if I'd spoken up.

  22. I was like your lady entrepreneur friend sounds like me! Except, I'm not at a place to hire yet, but I sincerely appreciate your advice to let go when you have to because I'm definitely independent to a fault. I want to echo taking care of yourself because chronic illness has definitely slowed me down. I tried everything and made a LOT of mistakes, which I don't like to call failures as you don't either as they all are for a purpose. But I'm happy to say I am closer than I have ever been to finally finding consistent health. A lot of it is the drive to finally create content that wants to burst out of me which all aligns with living my purpose as a mom and sharing my passions. Thanks again, Roberto, for another excellent video. You are a gifted speaker

  23. I think that is a good way of looking at it I might try that more when you said that either you win or you learn. When I was learning how to do stuff wether it was drawing or making videos It took me some time to understand that the mistakes are something I can learn from instead of thinking it was a loss or i couldn't improve from it thanks again for the helpful video.

  24. Roberto, I pray for your happiness and continued Prosperity. I think my biggest mistake is that I grab for the L instead of the W. I pray that I have the courage to go for the W…

  25. Getting help is very much needed. I'm always of the opinion of why tackle a task that may take me 12 hours to complete, when I could outsource to an expert who can complete it in 2.

    Self reliance is fine but letting go of pride and asking for help is better.

    Deep video. Great message.

  26. Much love and respect sent your way Roberto !
    Thank you for everything you do to help us!
    We all can relate in some way! Keep up the great work!🌍✌🏽

  27. Lol the problem is I don’t think I learned yet. Post college 9-5 is so different and so much more stable. Rejection is definitely a huge one, but I still don’t think there’s enough risk of failure to really feel bad about it yet, because I have a back up.

  28. Roberto, thanks for another great video! My biggest failure that taught me a valuable lesson is always making my job my #1 priority instead of putting myself on the priority list. I never took vacation days or rest days and I worked on projects when I was home. When I was laid off, there was so much resentment. I am glad that I learned this lesson early in my career than later.

    When I get a chance, I will definitely check out your podcast.

  29. Make this Blue If you love Roberto Blake and am a young yutbr with a Goal to get to 10k Your help will mean so much
    ⬇️ let's show ❤

  30. We love you Blake. For real. Your information is pushing my channel so quick its unbelievable. I appreciate you. Thank you

  31. This hit hard! Thank you for your transparency. I am at the cusps of forming a team going into my first salon space after being a solo stylist for 5 years and I NEEDED to hear this. Thank you 😊✌🏾

  32. Bro, I can give you a free, customized health & wellness plan. No joke. I’m launching my YouTube Channel in September before I head back to school (I have 24 videos prepped for 3 months worth of content). All I would need is your height, weight, age & all the different types of food that you enjoy eating from breakfast, lunch & dinner so that I can make the meal plan. I can email you the program. And no………. I’m not a bot dude

  33. I learned a lot from you. I’m looking to genuinely give back in regards to what you give us. Yeah, there are some good people out there.

  34. Hey Roberto! Could you please make videos about dedicated channel tips. Most often you talk about channel types like yours (talking to camera about different topics) and most tips from others also come about similar formats. I myself am sculpting channel – no face, simple voiceover on sculpting footage. Could you diversify like this and make tips for this type of crafting channels, and others as well like reaction, gaming, outdoor etc. Pretty sure there are many who has different formats like this

  35. my biggest regrets always come down to not doing stuff sooner! we all know life is short but sometimes it is hard to find the motivation! #doitnow

  36. 😀 The thumbnail for this video is AMAZING! The part about your friend was extremely helpful, thank you. Struggling with chronic pain myself I can relate with what was said, as well as learn from what was said. Thank you so much. 🙂👍🏽

  37. I've been wanting to start a business for a LONG time now and I STILL don't really want to trust others to work for me and actually do their job as it's to be done.
    However, I know I'll need to.
    I'll most especially need a lot of people to work remotely, from home. I know that means there will be things I'll just have to accept.

    I do know, at least as of now, I will not be hiring family/friends nor will I ever ask them for anything regarding business.

  38. With a mind of humility, we can learn anything…Great of you to share these insights Roberto…thanks for your advice and all your support 🙂

  39. Not getting started and quitting too early are failures I did. I always thought that it has to be perfect until I realized that done is better than perfect most of the time. I do not say that quality does not matter – it is crucial, but sometimes you need to hit that publish button and learn from your mistakes in future videos/articles. It took me way too long to getting started with my YouTube channel. Once I got started, I got moving, and everything became much more straightforward. It is still a lot of work, but walking is easier when you made your first step towards your goal.

  40. "There are some of you watching this, you find every excuse and every reason to snatch defeat from the jaws of victory."
    I didn't think that I could relate to this but I feel this is happening to me lately. I mean, I've become so good at these excuses that I can actually believe them.
    Many thanks for the slap in the face and for all these videos on personal growth and entrepreneurship. 🙂 Wishing you all the best!

  41. Love hearing the failure side to entrepreneurship. Everyone loves to show the success, the money, the fame, but there are not many people willing to be real on social media. Makes you so much more relatable and I think it is a great thing!

  42. You were right on Twitter. Definitely one of your best. Visuals are crisp, love the BG, sound quality is perfect; not diminishing the actual message itself…the honesty, man…this is real. This is why I love the channel too. You’re only getting better, dude.

  43. Thank you sensei for the wisdom. I've learned to never give up and push through the resistance like a rocket ship travelling to space

  44. I SWEAR you keep making these videos just for me 😉 You are constantly delivering the message I need to hear at the EXACT moment I need to hear it. THANK YOU…seriously, thank you!
    A lesson I was reminded of just yesterday was to stop expecting everyone to understand my dream. I recently decided to FINALLY start a podcast and recorded and edited the "intro" episode. I WAS SO EXCITED I decided to share with some family members. Of course (and I already knew this I was just drenched in excitment so I forgot myself) the reaction was lukewarm and flippant versus encouraging and supportive. I was pretty pissed at first but this am I had a long talk with myself and reminded me that I have to be my own cheerleader right now because the people in my real life can't relate to this right now…they don't understand why I'm evening dreaming these things. So I need to keep things close to the chest right now and SHOW them where I'm going.

  45. Not embracing the suck. I built that thing that my community needed and said was not able to be done. I burned out from giving continuously and not getting support from the community I was serving. If I had embraced this as an opportunity rather than getting frustrated and practically walking away, I would have seen the leverage for a successful opportunity I had created… now, I’m rebuilding a decade later but with a new perspective and better methods for experimenting with opportunities

  46. my most powerful life lesson was actually being very careful who you give valuable information to, as robern greene says 'never outshine the master' not many people seem to understand this, I get sick of entitled people who think after learning just a few bits of information they already think they're masters, so they use you or try and use you for information then ditch you at the first opportunity they get.

  47. Man this is insightful, I have the same issue. I do it all myself, and I have zero plans of ever adding anybody to help. To meIt would be amazing to be that guy with a massive following who does it all on his own. I will be mindful of your advice on this one, and I appreciate your insight. FYI Roberto your thumbnail is sick! You should print that thing out on a poster and hang it on your wall.

  48. I learned – the hard way – that when that little voice in your head says "run away" from a potential client, no matter how cool the project is, RUN! Some people are such a pain in the ass to work with that no amount of money is worth it. And usually those people will end up stiffing you anyway.

  49. We all have made mistake. I have invested in things I wish I could have taken back. I have laughed at myself for being so stupid sometimes. I have learned and I am sure I am a better person and investor now. God Bless my bro

  50. Always prepare to deal with unexpected circumstances.. biggest thing I've learn in my journey. Nothing goes exactly how you plan it.. #championsadjust

  51. This is do fantastic!!!!! You are speaking to me in so many different ways!!!!!!

    Just adding a team and am finding I wish I had done this a few years ago!!

  52. Roberto, side question. Is teespring better than making the shirts and shipping them on your own? Because it’s more passive? But less profit?

  53. This is great advice! This is what I gathered from your video-seek help. Enlisting others will provide alternative solutions and vantage points.

  54. Wow – Love this perspective! Can totally relate to the idea of “staying solo too long”…. I’m also learning to focus time/attention on what’s most important, be resilient and learn from my failures, AND have the humility to trust other people enough to be able to delegate. Thanks as always for sharing! xWBW

  55. My biggest mistake is being deflated that my channel wasn’t growing at an exponential rate when I knowingly and intentionally started a channel covering a niche subject.

    I need to remember that I will vibe with my tribe, no matter how small.

  56. I totally get this. My problem; I have tried bringing people on to help me a few times and it works for a while, but then I find I start picking up their slack and eventually the people who are supposed to be taking some of the work load off my back are adding even more work to my plate. I don't know if it's because I have unrealistic standards, but I figure if I can do something with 10 other things on the go, why can't they do something with nothing else on the go? And then I get frustrated. Now every time I work with something I fear it will end the same way. I know there are some great people out there that I could work with, but finding them, or training them to help the way I need them to has been a struggle. any advice on that?

  57. Solopreneur works in the beginning but there's a tipping point where the only way to scale is to leverage other peoples time. Definitely don't need to bring in people at the start but learn to recognize when it's time to build the team. Thanks for the vid.

  58. I've been saying I need help for the longest time to achieve what I want, its too much for me alone. I'm trying to reach out, but my biggest thing holding me back is the nagging thought of "why should this time be different?"

  59. Great content Roberto. I'm similar to your friend in that I was forced out of a traditional workplace due to chronic illness and need to make a path for myself. Glad to hear this reason being acknowledged.

  60. What I would really like to know and what boggles my mind is, who the heck are these people that are giving you a thumbs down? It's insane. Roberto, you're one of the most sensible and thoughtful persons I've come across on the Tube by far. Man, you're always pushing out positive vibes and trying to help folks. I just don't get it.

  61. I can relate to so much of this. Therapeutic to listen to. Thank you for always educating and inspiring whilst keeping it real.

  62. The only way to learn is through failure! Amazing to see that you've learned so much from that experience, and are working forward from it

  63. I LOVE this thumbnail! Your videos have been some of the most helpful for me as I work to figure out this “YouTube thing.” Thank you 🙏🏼

  64. I love this new style of video. It feels more real and overall it makes you more relatable. These videos make me feel that I can like I can achieve my dream of doing an online business. It helps me because I understand I don't have to be perfect to make it. Thank So much🙏🏼

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